aspirin project

6

i have weird as level chemistry project where i have to make aspirin from willow bark but the the only thing i found after research is the synthesis of aspirin from salicylic acid not willow bark, after admitting defeat i went to chatgpt as a last resort but that did tell me the process a little but since the answers are so vague i try to ask in detail but it start changing information so anyone could help me with how to do it or provide me the steps with what equipment and chemicals of what concentration and how much of it , i would be very thankful.

Reply 1

Nitrotoluene

12

Original post

by snow06

i have weird as level chemistry project where i have to make aspirin from willow bark but the the only thing i found after research is the synthesis of aspirin from salicylic acid not willow bark, after admitting defeat i went to chatgpt as a last resort but that did tell me the process a little but since the answers are so vague i try to ask in detail but it start changing information so anyone could help me with how to do it or provide me the steps with what equipment and chemicals of what concentration and how much of it , i would be very thankful.

I cannot suggest anything more than that in accordance with the TSR regulations.

The first step is to get salicylic acid from willow bark. Remember to squeeze the bark very well and, collect the liquid and after filtering it, mix the baking soda solution for neutralization of filtered liquid. The next step is to heat the mixture until a white powder is formed; the precipitate is salicylic acid. Then, combine the salicylic acid powder with acetic anhydride and a drop of concentrated sulfuric acid. Stir everything together for around 15 minutes, use a magnetic stirrer possibly. Next, cool the mixture in an ice bath and thereafter, transfer it into a large beaker to get a white precipitated, this is aspirin. When the white solid aspirin is filtered, rinsed it with cold water gently, and dried away from water (possbly in a vacuum stove), you obtained your product.
EDIT: Simply squeezing the bark will not release the entire starting compound. For more effective extraction, it is best to soak the chopped willow bark in hot water and leave it to macerate.
Krgds,
Sandro

(edited 8 months ago)

Reply 2

TypicalNerd

18

Original post

by snow06

i have weird as level chemistry project where i have to make aspirin from willow bark but the the only thing i found after research is the synthesis of aspirin from salicylic acid not willow bark, after admitting defeat i went to chatgpt as a last resort but that did tell me the process a little but since the answers are so vague i try to ask in detail but it start changing information so anyone could help me with how to do it or provide me the steps with what equipment and chemicals of what concentration and how much of it , i would be very thankful.

My understanding is that willow bark contains a lot of salicin, which hydrolyses and later enzymatically oxidises to salicylic acid in the body without ever actually forming aspirin (acetyl salicylate), so I don’t think it’s possible to extract aspirin from willow bark directly - you would have to chemically transform the product, which I expect you’ll have some difficulty with given the awkward reactivity of the functional groups present in the desired hydrolysis product (salicyl alcohol).

You could probably try grinding up the willow bark and then heating it in a 2 mol dm^-3 hydrochloric acid solution for an hour or so to get an aqueous solution of salicyl alcohol (and a load of other junk) but I would think oxidising it to salicylic acid using a potassium dichromate solution might prove awkward as the phenol group can be oxidised to give benzoquinones. You’d probably have to atmospherically oxidise it, which would take ages.

aspirin project

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