The Fischer Esterification: Methyl Salicylate

Hi everyone and welcome back to the lab. In this video I'll be highlighting the fisher estrification reaction by making methyl salicyate. Uh is actually a very important organic reaction and it's extremely common for undergraduate students to do this very reaction um as part of their studies. It was discovered in 1895 by Herman Emil Fischer of Fisher projection fame if you've been through your kirality unit. Um and also co-discovered by Andrew Sch who is less credited for this because the FisherPire estrification as you can clearly see is hard to say. Anyway, those silly Germans um anyway they came up with this reaction where they noticed if you mix a caroxilic acid with an alcohol under acidic conditions they u they join together to form this compound here which is called an esther. Um what happens is that under acidic conditions these carboxilic acids can be protonated on this oxygen here and that proton here sort of disrupts the electrostability of this network here and you end up with an oscillating double bond across those two. Now that oscillating double bond in the process of switching uh leaves a tertiary positive carboation right here in this uh in this center here which is subject to nucleophilic attack. The hydroxal group being a decent nucleophile works its way in. The alcohol ends up attaching itself right there in the crutch of the caroxilic acid. Um you lose this hydroxil as water and you end up with the esther. It's very basic reaction and it's extremely important as I mentioned because esters make up the vast majority of what you can taste and smell in fruits and things like that. So, uh, you know, wines get their fruity aroma from esters, um, whiskey and things like that, rum, uh, all sorts of fruits and vegetables. The artificial flavorings that mimic fruits and vegetables, the vast majority of them are esters. Everything you can smell in perfume, flowers, things like that. So, they're extremely common compounds. They're not very toxic, and as such, it makes for a good undergraduate preparation. The reason this is such a neat reaction is that salicylic acid is basically odorless. It's a white crystallin solid and methanol doesn't really smell like much either. It's sort of weakly alcoholic. Doesn't smell nearly as much as ethanol. Anyway, when the two come together, you get methyl salicyate, which smells extremely strongly of wintergreen. In fact, it's the primary constituent and oil of wintergreen and it's used at flavorings for wintergreen candies like Lifesavers and things like that. Wintergreen gum, you name it, methyl salicellate is probably in there. It's also used on in some things like Icy Hot where you rub it on your skin and the salicylic acid um you might notice as a uh as a derivative. It's the hydrayzeed derivative of aspirin which is a settle salicylic acid. So if there's another one of these caroxile groups attached here at this oxygen that would be aspirin. And in fact the active ingredient the non-steroidal anti-inflammatory drug or NSAID for short in aspirin is salicylic acid. And uh it's the formation of salicylic acid by the hydraulysis of aspirin in your body that uh that has the effect. So as such methyl salicyate is used a lot in topical ointments that are designed to relieve pain. although uh double blind studies have shown that it isn't quite as effective as many people claim it to be. Anyway, let's go ahead and make some methyl salicyillate. So, I've gathered here the materials necessary for the reaction. We have here the salicylic acid which you can see is a chunky white powder. Uh this is 27. 6 g of salicylic acid which is a 2 molar scale which is what I'm running this reaction on. This is 30 ml of methanol. Now, this represents about a four-fold excess of methanol, and that's necessary because methanol also acts as a solvent for this reaction. You don't have to use excess alcohol as the solvent, as I'll demonstrate in a later video. Um, but methanol in this case makes an ideal solvent for this particular reaction. And so, I'll be using it here. And then finally, we have this, which is 10 ml of 93% concentrated sulfuric acid. It's just drain cleaner, but uh that will serve as our acid catalyst to facilitate the reaction. I'm going to start by taking a 100ml flask and placing a small stir bar in it. One that's suitable for its size, of course. And then I'll begin charging the reactants using a nice uh jointed powder funnel for this. First, the salicylic acid. Needs a little poking with a stir rod sometimes cuz the uh the chunks tend to clog this funnel. The reason why I'm adding the salicylic acid first is because when I add the methanol second, I can use it to wash the salicylic acid out of the funnel. All right, here goes the rest. And now I will add the methanol to wash out the funnel. You can see the flask is just about the perfect size for this scale. Now the third ingredient, the concentrated sulfuric acid will react with this to uh generate heat which will be slightly violent because the methanol isn't perfectly dry and the sulfuric acid isn't perfectly dry either and neither was the salicylic acid. So um remember the saying do as you order, add acid to water. It's the same sort of thing. If you're adding a concentrated acid to anything, just make sure that you put everything else together first. Uh which helps absorb that heat.

So, I'm going to pour that straight down. And you can see a small amount of heat has been generated and the methanol has begun some localized boiling which will settle down very shortly. Also remember that when you finish using a cylinder for something like concentrated sulfuric acid, remember to always rinse it out right after because if you leave it out on the bench and someone doesn't know, even if they pick it up on the outside, there's a little dribble that runs down and uh concentrated acid is no fun on the skin. So just for safety and always, of course, wear your safety glasses. All right, I'm now going to set this flask up for reflux. I'm going to uh lower this clamp into the heating mantle and remove the funnel. Remember, this has concentrated acid in it as well, so it needs to go in the sink and be rinsed right away. I'm going to fix a 200 mm live condenser vertically and secure it with a clamp. And now I will start the stirring followed by the heating. And pretty soon this will come to reflux. Now of course the purpose of refluxing something is to keep it at the highest temperature possible uh for a long period of time. And of course the highest possible temperature this solution can be without leaving without any of the reactants leaving that is the boiling point of methanol. So this will heat up to about that temperature. the methanol will boil out and end up in the condenser where it will drip back down. We'll bring this to a boil and let that happen for about an hour and a half while we talk about the uh the rest of the workup of this reaction. Um I'll discuss that briefly before I do it and uh we'll come check up on this in uh in a little while. The workup of this reaction is actually fairly simple. I'm going to draw a container here and this will represent the reaction flask contents of the reaction flask when the reaction is over. Now, since this is an equilibrium reaction that involves the removal of water and during the reaction, we're not really removing any water, um it's mostly just being sequestered by the sulfuric acid. Um that means that there's going to be a significant amount of the starting products left uh within this flask in addition to the final products. So, I'll list them out here. All right. So, you'll notice we'll have methanol, sulfuric acid as the catalyst, methyl salicyate, salicylic acid, and water left in this flask. Now, how do we separate those out? Well, the first obvious thing becomes uh boiling point, right? We maybe we could fractionally distill this some amount. And that is true to some extent. Methanol boils at like 68 something Celsius. Maybe it's 70 something. I don't really remember, but methanol boils at a very low temperature. Certainly much lower than any of these, even water. So, by heating this, we will be able to drive off the methanol and take it out of the equation. Um water will leave it about 100. We might be able to remove some water by heating it to 100, but remember that sulfuric acid has a very high affinity for water. And so, that's going to artificially raise the boiling point of this whole thing. and we may end up destroying things if we try and drive the water off using this method. So now we need to find a way to separate these components. We've removed methanol and the solution here is to add a base because if you look at the solubility of methyl salicyate and water, it's not very soluble. Salicylic acid is also not very soluble in water, but sulfuric acid is and obviously water is. So if we were to add water to this solution right here, we'd end up with layers like that. the methyl salicyate and salicylic acid would end up in the top layer and the sulfuric acid and water would end up in the bottom layer and we'd be able to separate the two. Now, there's something interesting that you can do to eliminate the salicylic acid as well. It turns out that salicylic acid is not very soluble in water. But like most acids, the salt of the acid is much more soluble in water. So if instead of adding water to this we add say a solution of sodium hydrogen carbonate or sodium carbonate or some other base like that would react with the salicylic acid to form sodium salicyate which would end up in the water because it's far more soluble in water than it is in sod in methyl salicyate that is. So that we'd end up with a layer of methyl salicyate which we can take right off and the rest of the components in the bottom. It's a quick extraction right? Well not so fast. If you look at the density of methyl salicyate, it's about 1. 1. The density of water is 1. 0, but you have all this crap dissolved in it. So, it's probably going to be like, you know, 1. 1 plus. We'll just call it that. I can't I can calculate it if I wanted to, but we'll just speculate that it's going to be close to this. And because these close densities, um, these layers aren't going to form so well. This might be on the bottom, could be on the top, but most likely it's going to form an emulsion, which means a tiny or a series of tiny blobs that are suspended throughout. It basically just makes the solution look cloudy and it's difficult to separate. And uh so we may have to do an organic extraction on this, which is we'll just add something like to the flask, right? The tuine will

layer out on top. Now the methyl salicyillate being fairly non-polar which is the reason it's not in all of this will migrate to the touine layer and everything else will stay in the bottom and then we can go ahead and take that layer off and then we'll end up with a you know a container of the methyl salicyillate and tuine only and then the tuine having a much different boiling point than methyl salicellate I believe it's around 130ish C not really sure but I know it's really far from methyl salicyate which is something like 222 they should be easily separable by distillation leaving us after the tuine evaporates with nothing but methyl salicyillate. So that is the plan. And as you can see, the mixture has now reached a stable state of reflux. It's uh only about uh 2/3 of the way up the condenser, which is pretty darn good. And it's returning it nicely. So I'm going to leave it like this for about an hour and a half to allow the reaction to go to go as far to completion as we possibly can get it at this temperature. All right. Well, this has been reflexing for approximately an hour and a half, and you can see that uh the color really hasn't changed. However, the consistency has. I'll show you that in a second. Of course, we're still reflexing away. There's a bunch of condensation on the condenser, as to be expected. It's humid here in the summer months. So, I'm going to turn off the heating and stirring. And I'll drop the heating mantle. Apologize for the squeaks, but you'll notice something has changed uh dramatically in that we now have a bifphasic system. And one of those phases is going to be the methyl salicoxilate, likely the uh denser phase at the bottom. And the upper phase is likely to be the methanol with sulfuric acid in it. So you can see there we've already got some pretty decent separation, which uh was sort of unexpected um as far as what I had predicted. But anyway, uh should be fairly easy to separate. So the first thing obviously is to distill off the excess methanol. So, I will let this calm down and cool down sufficiently to stop boiling and then switch over quickly to a uh a different condenser and we'll be able to start stripping some of the methanol from this. All right, so as you can see, I've got this set back up for distillation. I just now turned the heating mantle back on. We have our cooled reaction mixture down there. I have a short path condenser attached to that just for convenience. Um, in general, you wouldn't use a short path condenser with methanol because the short path uh doesn't condense the methanol vapors fully. However, I'm not really going to be collecting the methanol. I'm just going to have it drip uh into a beaker. I'll put that up on another labjack or something. Um just because I'm not reusing the methanol. Believe me, anything that comes in contact with methylate will stink like winter green forever. So, there's no way I'm actually going to uh be able to purify this methanol enough to put it back in my stock, rotate it back in as say washing methanol. So, uh anyway, I've just turned heating on. Like I said, pretty soon the methanol will start to uh condense in this condenser. We'll strip it off until the uh the methanol is gone. At which point we'll notice that it'll be harder to boil. Um and the mixture will get a lot more viscous. And when we start getting mostly water rather than ethanol out the end here, uh judging by just how it's dripping in the beaker, looking at the liquid density and things like that, honestly, we can just ballpark it. We're trying to remove most of it, not qualitative amount here. Then uh we'll proceed to cool it down and go to the basification step. While we're waiting for that to boil, I'm going to go ahead and prepare for the basification step by making a saturated solution of sodium carbonate and water. So, this is sodium carbonate. Um, it's pool pH plus. Of course, it basifies your pool, so it raises the pH. Um, and it's sodium carbonate monohydrate, almost completely pure. And it's so cheap that I really don't care to measure it out to actually make saturated solution. I just make sure I add enough that uh it's not all going to dissolve. Doesn't really matter if there are impurities in this because again or it's staying with the uh aquous layer anyway. If it dissolves and if it doesn't dissolve, it'll be decanted. So, no big deal. I'll just continue to stir this until uh it's dissolved. And if it completely dissolves, there's nothing left on the bottom, I'll add a little bit more until some remains on the bottom, indicating that the solution is saturated. All right. Well, you can see the methanol is starting to come over. Um, I've added some foil around this flask because the geometry of the short path condenser doesn't really allow me to uh center the flask in the heating mantle. So, the foil sort of helps keep the heat in. It's a good trick to have that around. Um, you see the methanol is slowly collecting here in this beaker. And we should be able to collect just over 20 ml, assuming we haven't lost any out the top of the condenser before, but I'm assuming we have. So we'll essentially just distill this until the uh dist distillation rate stops which means that the flask is now transitioning to distilling say water or something other high boiling point which will take uh quite some time. So we'll definitely notice when this slows to a halt at which point we can stop this and then head for the basification step with the sodium carbonate which is still dissolving. All right, but it looks like we're not really going to get much methanol out of this. Uh we've got about 10 milliliters and uh the distillate is starting to smell strongly of methyl salicylicate

now. And you'll notice that the film that was on the glass here has gone away and it's now sort of given way to wispy white vapors. Also, if you take a spot sample of the liquid coming out here and you evaporate it, you end up with this residue here, which is an oily substance which is consistent with methyl salicyate. Really smells like oil and wintergreen. We've pretty much removed all the methanol and we've now gotten into the stage where we're volatilizing the uh the product. So, I'm going to go ahead and stop this now by turning the mantle off. And uh I'm going to lower this down to reduce the heat. Then we can go ahead with the basification step once that cools, of course. All right. So, this has had a chance to cool. It's now just under boiling. It's probably still uh 70 or so Celsius. In fact, I can check that right here. Yep. Wow. I was right on the money. 70. 6 Celsius. So, still fairly hot, but it's uh it's cool enough to handle at this point. And of course, since uh the methyl salicellate doesn't boil at 222 Celsius, it's not particularly volatile at this temperature. Although, it will uh stink up the lab as it normally does. Um it's nothing that we can't handle. So, I'm now going to pour this into a uh small beaker here. And we will use the speaker for the neutralization process. Um you'll notice that it is still by phasic. And actually I was uh pondering this while it was cooling. And um I think I've come up with a solution. Uh the thing is we accidentally did two steps at once in the first step. The reflux condenser I chose was not as efficient as I had assumed uh for methanol. And despite methanol condensing rather uh well in the condenser as you might remember um we were losing some off the top or it was reacting. So um what happened was the uh methanol was slowly escaping from the system while some other methanol was reacting and eventually uh there was so little methanol in here that there was nothing to keep the two layers mixed together and that's the role that the methanol would have played before because remember after we remove the methanol we expected it to be bifphasic and then uh we can move the salicylic acid from one phase to the other with the neutralization procedure. So anyway um I believe that's what happened. It's also why I got so little methanol out before it started switching over to uh the salicylicate. So anyway, that explains everything. Uh experiment is still on track. I'm now going to uh transfer this and uh into this beaker and we'll proceed with the neutralization procedure. All right. So now that we have the mixture transferred to the beaker, I'm now going to begin the neutralization process, which will force the salicylic acid into the aquous layer. This is the sodium the saturated sodium carbonate solution. There's some gunk floating in it, but we'll remove that later. Um, and it's cloudy because of course it's saturated and it cannot hold anymore. And as it slowly cools, uh, tiny amounts of sodium's uh, sodium carbonate are precipitating out. Anyway, I'm just going to add this uh, to the speaker until the fizzing sort of slows down. And then I'll keep checking it with this uh, book of pH paper here. You can get this for cheap. I think I got it for like 20 cents a book uh, on eBay from China. So, I picked up a huge pack of these, like, you know, 50 or 60 bucks. So, uh, very handy to have around cuz obviously you never know how many times you're going to need to use it. So, I'm going to go ahead and start adding this very carefully. Oh, yes. Localized heating. Lots of fizzing. It looks like gas production is slowing down. You can tell by uh when it foams back up when I start stirring it. Um that's because that there was insufficient mixing to uh successfully get the two to react before. So you can see it's much less violent now. Still not quite neutral as you can tell by the bubbles, but uh we'll check it with our pH paper. It should show uh still uh fairly acidic. Yep. So you can see that's oil the wintergreen on top. That's the methyl salicyillate and then that's the actual uh the actual solution there underneath. So it actually is layering out fairly well. I did not expect that. I guess the densities are more different than I'd imagine. Now we're getting very close. And strangely, the solution turned orange. I bet that's because it's becoming basic. And there's probably some iron in that sulfuric acid. Yep, it's got to be. So, it's probably some iron hydroxide, which is not a big

deal. I'll use the other side of this uh piece of pH paper. See if I can get up a little bit of oil. Yep. And you can see now that we are somewhere on the basic scale. If you look through the oil, which has contaminated the paper. So, okay, we've successfully basified that. And if you look, let me bring my camera down and you can see here how it's still bifphasic despite uh the neutralization. So, even though we guess that the densities would be fairly close, they are in fact sufficiently far apart that the metal salicy is floating on top. That also means that it's methyl salicyillate has a density of 1. 1 and the solution down here has a significantly higher density than that which was probably aided by this sodium carbonate solution that we added. So anyway, I'm going to uh go ahead and put this in a set funnel which I have prepared uh just over here and uh we'll go ahead and take that top layer right off. All right, so this has now cooled down and you can see that the emulsion has gotten a lot worse and this is because the solution has cooled down. uh things like sodium carbonate have precipitated out sodium sulfate perhaps and also more of the methyl salicyate and the densities of these two are so close that uh the emulsion is uh staying happily together. Now we're trying to get at least one of these layers clear preferentially the upper layer and you can see that either of these are so we're probably going to have to resort to the organic extraction method uh that I outlined earlier when we talked about the isolation scheme or the workup scheme as they call it uh for this video. Now, um I can work it up with a number of things. Ideally, dil ether would be used because the dithl ether boils at a very low temperature and will be the easiest to um remove from the methyl salicy when we're done. And it's great because it has a very low density. So, it'll float on top and it's just going to only help the methyl salicyate come to the top as it dissolves. Now, uh I chose something like talluine because I don't really have a whole lot of dthyl ether at the moment. And tuine has the density requirement. It's good. It's very low density solvent, but uh unfortunately it also has a high highish boiling point of 130. And we just noticed that when taking some methanol/water off of the reaction mixture, we were getting a significant portion of our product with it. So I'm kind of apprehensive about using talluine because um it appears that methyl coat is still with it to a great extent. So uh my other option is to use dchlorommethane which is risky because remember this is density 1. 1. So this is a higher density than that, probably somewhere between 1 and two. Um, and dchlorommethane has a density of about 1. 3. So this could very well be about the same density as dchlorommethane, which would leave us in the same emulsified situation that we've been in. So what I can do though is h take a small amount of the uh of this out of representative sample and put it in a small tube and shake it up with some tuormethane and see if that actually helps the situation or not. So, I'm going to go ahead and do that. Question is now, does the dicchlorommethane go to the bottom? So, if it does, we're in luck and we can do that on the large scale. If it does not, then uh we're going to have to rethink what we're doing here. Actually, it looks like we're in luck. Notice it's collecting at the bottom in a nice clear layer. And uh that is exactly what we want to see because the methyl salicyate will have moved into there. Okay. So I know we can go ahead and extract this with dexane. So pour this back in here and so not to waste anything. And I'm going to go ahead and add um several portions of dchlorommethane to this. Maybe 30 or 40 milliliters at a time. Just enough so I have room in there to shake itself. And I'm going to go ahead and remove the uh stir bar if I can get in there. All right. So, protrude to stopper. And you can already notice that there's no more organic layer at the top. It's all at the bottom. So, the methyl salicyate has completely migrated to the dchlorommethane layer. And uh as you can see, it's already being very efficient at extracting this. So, that makes me happy. Let's just invert this a couple of times venting often. And uh then we can go ahead and uh get the organic layer in a separate container and then separate the methyl salis away from it. Just in time there. See the vapor pressure of that chloromthane is significant time I shake this. It wants to explode basically. It's just another reason why you got to wear safety glasses because that if it was inverted for more than a second longer it would have sprayed everywhere. All right. So, now that that's been shaken a few times, I'm going to clamp it back in and let it settle. After sitting for a minute, you can see it's got a nice clear layer. So, I'm going to go ahead and drain it into this fresh beaker here. Oops. I need to stop in order to drain it, of course.

There we go. And now uh we'll do one more rinse with the dicchlorommethane. And I'm going to call that good. This going to be a slightly smaller portion. And again inverting venting often. All right. So, here in the speaker, we now have dchlorommethane with our product, and we just need to separate the two. And they have very different boiling points. So, that's very easily easy to do uh by distillation. I'm going to try and clarify this a little bit uh by shaking it with some calcium chloride. Although, yeah, it looks like there's enough iron particulates in there that it's not really going to matter. I'm gonna have to distill the uh the methyl salicellate anyway. So, I'm just going to pour this right into a flask. Here we go. It's a nice 250. And uh go ahead and distill them to separate. All right. So, here is the setup. I've set up, of course, for simple distillation with a short path condenser, which is necessary this time because what we're distilling has a very high boiling point of 222° C. will monitor that with this thermalouple which is stuck down a glass tube with a closed end. Um there's a thermalouple here. 24. 9 in there. 24. 9 in the room. Kind of hot up here sweating today. Anyway, uh got the heating mantle. We go turn that on. We'll get the condenser water going. And of course uh in the flask is the mixture of dchlorommethane and methyl salicyate among impurities uh like a bit of water. So what's going to happen is uh that'll start to boil. We'll collect all the dchlorommethane first and we can verify that by the temperature. We will then start to collect water. We can also verify that by temperature and maybe some methanol actually before all of that even. But most importantly um near the 200ish C range we should start collecting pure methyl salicellate. I may need to cover this with foil to uh get to that temperature. And I've braced for that by using a stainless steel cut clip because these will melt. Anyway, the short path condenser is well suited to handle compounds with high boiling points. And uh when that happens, I will switch out to uh a smaller flask here, which I still need to, you know, flame dry basically. And uh we'll collect the metal salicylicate in that. So uh yeah, heating is on and uh keep you posted with updates. All right. Well, I started heating fairly violently and most of the dchlorommethane was gone pretty rapidly. The uh short path is having a little bit of a hard time keeping up. You can see by the wavery solvent vapors coming out of that tube there. But uh I didn't expect it to catch all of it anyway. It's not a particularly efficient condenser for things that boil at that low boiling point. Uh the temperature is now climbing somewhere between dchlorommethane and water, which is good. It means we're removing both. And pretty soon we'll be left with nothing but a whole salicyate in there, which uh will come over at 222 C. So I'm going to swap out this flask for the smaller one, obviously somewhere between then. And uh so maybe around 180 Celsius. I don't know. It depends. But uh that said, I should mention that this experiment smells quite a lot. Uh obviously metal salicyate is oil of wintergreen and it's on my gloves and everything. And man, it smells like someone chewed like 80 packs of gum and stuck it all up under the table. It positively stinks in here. Well, here I am waiting for some dchlorommethane to distill off of methylate. And what do I find on top of the solvent stock sitting on top of a gallon of acetone? There's a toad. Come here, buddy. Oh. Oh, he's a sticky little fella. Oops. Don't run. Oh, there he goes. He escaped. Well, he's down there somewhere. I'll have to go capture him in a second. Well, I got him. Look at that. There's a specimen. What a strange thing to have just suddenly end up in your basement. No matter which way I turn the jar, he keeps looking the same way. He's trying to go toward like the darkness or something. It's like a tree frog or something. He's really uh sticky. There, look. There you go, little buddy. You be safe. Stay out of the lab, will you? Anyway, back to nonfrog related activities. Uh you'll notice that this has substantially decreased in volume and there's also some methane collecting in the bottom there as expected. Of course, um the theoretical yield for this procedure is something like 30 g of

methyl salicyate, which at a density of 1. 1 is about uh like 27 uh millit. So out of this 250 ml flask, it's not going to look like much. Um and it'll fill theoretically if there was 100% yield um about a fifth of this. So it's not really going to be a whole lot. Not expecting a whole lot. We're getting close though. So, I'm going to start monitoring the temperature and the drip rate uh very closely. All right, I've got a mysterious high boiling liquid beginning to climb. It's right in the joint right now. Suspect that might be the methyl salicellate. Still at only 44 C on the uh thermometer, so it could also be water, but judging by the wispy vapors up front and uh the way it's rolling down, I don't know. Maybe it is water. It does have a pretty high surface tension. We'll know as soon as it hits this. If it fling if it flies past 100 C when it touches the thermometer, then uh we'll know for sure and I'll be able to uh swap that flask out. All right, it's touching right now as you can see. So, this is going to obviously start to climb very rapidly. I'm actually going to regulate this back a bit. Um, so we can do the swap in relative piece. 97 102 107 114. Yep. We are ripping past water. So now is the time to swap the flask. Time is of the essence. 150 160. Yep. Let's go downward. Vapor still hasn't reached the condenser yet. Pop that off. Go down a little bit more. All righty. And I'm going to wait. Yep. See, we're at 209. Yeah, we're coming up on the methyl salicellate for sure there. All right. Full four again. We're going to wait for the first drop to fall. And they're starting to fall now. Five. six drops. All right, we're going to stick this on. Those first drops will clear the uh remnants of the chloromthane out. And uh as you can see, we've managed to time that perfectly. And we're now collecting pure methyl salicyillate. That beautiful nice oily, completely clear liquid coming over at uh 217, but it's still equalizing theoretical 222. All right, we're nearing the end of the distillation. You see there's still vapor's pouring down. Uh the drip tube is uh it's blocked now, but so it's uh it's not dripping actively, but it's still filling up. Still taking it off at uh you know 222 223, well within the boiling range. Um but we're slowing down now and before I char the crap out of this flask, um this is going to start slowing down and I will uh quickly stop the distillation before it runs completely dry. And that's the benefit of having a lab jack underneath all this stuff because you can just lower it down and uh essentially remove the heating immediately. Oh, there. See? Now notice there's no more methyl salicyate coming over just none. That liquid in there must not be metal salicyate. So that means we're done collecting and drop the mantle. And look, it's uh basically bone dry. All right. Well, that is a successful distillation. Whatever is climbing the flask there is clearly not methyl salicyate. It's probably uh some other esester or something that may have been formed on the side hydroxil or something like that. And in here we have our pretty much pure methyl salicyate and that looks to be in great yield. We expected that to be 1/5 full to get a 100% yield. And honestly, that is really close. But uh I'm going to go ahead and put it in a storage jar over here. Uh but I'm going to tear the bottle so that I can figure out exactly what our yield was. There's our salicyellate yield pure methyl salicellate. That's quite a bit, too. All right, the bottle weighed 68. 5 g. So, survey says our yield is 25. 2 grams. Uh, that's really good. That's like 85% yield. Uh, theoretical yield is something like 30 grams. So, that's really, really good. Well, we did uh we did excellent on this one. Well, that's about all I have for today on methyl salicyellate. I hope you enjoyed the video. If you did, please press the like button and subscribe if you'd like to see more videos. even more videos, um I do have a Patreon account. Link is in the description. If you'd like to donate 50 cents or a dollar or something like that toward uh making a video, uh that would be extremely helpful. That's what helps pay for salicylic acid and methanol and glasswware and all sorts of stuff

like that. So, every little bit helps. If you can contribute, I thank you very much. And there are several rewards. You'll get your name at the end of a video and things like that. Anyway, thank you very much for watching.