Laboratory Synthesis of Aspirin

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With some important techniques under our belts, let's try our first organic synthesis! The target will be aspirin, which was first synthesized in 1899. It's just one step, and it's as easy as synthesis gets, so it shouldn't be too hard. And we get to put our newfound skills with filtration and recrystallization to the test!

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I made Asprin in my Organic Chemistry Class in Uni. I snorted the "white powder" as a joke I was then told to leave the lab by the lab tech/TA. A week later I was removed from the class and I had to take it the next semester.

badbotbit

I can still remember a reaction I performed in organic chemistry that kept me up into the late hours of the night. I had done the reaction perfectly and all my numbers and reactions appeared to be perfect. The damn thing would not come out of solution. So I’m looking at a pure clear liquid that was holding within, my product. Tired and impatient I dumped the ethanol fluid into a test tube and stuck it into the freezer. Nothing. I then remembered how super concentrated fluids need a seed to begin crystallization and the same is even true of snowflakes. With a spoon I made tiny scratches on the bottom of the tube. Not only did my product come out of solution, it came out as perfect little rectangular prism crystals, no more than five. I could only use a melt test, but it came out at a very pure temp with well over a 95 percent yield by weight. Everyone else had only managed to produce a powder with much lower purity and yield, I never spent longer on an organic chemistry reaction than that experiment and I never got better results. I was Jessie Pinkman years before breaking bad.

BenjaminSteber

Neo (waking up from a training program):
"Whoa, I can synthesize Aspirin!"

Morpheus:
"Show me. I've been a tad headachy today."

grimcity

I'm on Aspirin for my heart. This is fascinating too me, thanks Dave!

NobodyI

one of the first lab experiments I recall doing when I took ochem as an undergrad. And pretty much the only one I recall going smoothly :P

thomasneal

I did this lab and it became much more complicated than it had to be. It started off the reaction of salicylic acid with acetic anhydride. Crystallization begins. Great, and from the looks of it, a high yield too. One of our people takes a sample to do melting point. Then we begin adding T-BME for recrystallization. After over 40 mL of ether, it’s… not dissolving. But then we notice that the ether is a bit discolored. And then our guy who’s doing melting point analysis says the MP is off by 12°C. We realized that our product was so impure that the aspirin had in fact dissolved and the solids left over were the impurities. So after carefully pipetting off the dissolved aspirin and putting it in a separatory funnel with water and DCM, we finally get our solution, put it on an ice bath, and end up with an experimental yield… of 7%.

bunsenn

we legit have to do this next monday in preparation for this semester's ochem lab lmao this is so surreal

apescape

I remember this from a 1st year organic chemistry practical 25 years But it was really fun.

NicolaasRoets

Very interesting, now I am going to look up and see if I can find how aspirin on an industrial scale.

JoeFromDetroit

Excellent video, it really teaches lab techniques. Most chemistry videos are just for entertainment. Well done!

ricardoserra

Arguably aspirin's anticoagulant / blood thinning property and use for heart attacks are more relatively significant than its use as an analgesic or antiinflammatory.

natureabioros