What chemical reactions are involved when aspirin is treated with ethanol and sulfuric acid?

Question

What chemical reactions are involved when aspirin is treated with ethanol and sulfuric acid?

Answer 1

Asprin has a carboxylic acid function group on it, and whenever you add ethanol to a carboxylic acid, along with a dehydrating agent, you get an ester

I can't be bothered drawning the structual formulae for asprin, get it from here http://en.wikipedia.org/wiki/Aspirin

And just change to carboxylic acid group into an ester with a 2 carbon chain on it.

I need to draw it but i can't, but you should be able to figure it out.

Answer 2

Esterification between Carboxylic Group of Aspirin and Ethanol ( catalyzed by Sulfuric acid ).  

CH3CO-O-(C6H4)-CO-OH [ Aspirin ] + C2H5-OH  ---- >  CH3CO-O-(C6H4)-CO-O-C2H5 [ Ethyl ester of Aspirin ]          

Trans-Esterification between Acetyl Group of [ Ethyl ester of Aspirin ] and Ethanol ( catalyzed by Sulfuric acid ).    

CH3CO-O-(C6H4)-CO-O-C2H5 [ Ethyl ester of Aspirin ] + C2H5-OH  ---- >  CH3CO-O-C2H5 [ Ethyl acetate ] + HO-(C6H4)-CO-O-C2H5 [ Ethyl ester of Salicylic acid ]          

Trans-Esterification between Acetyl Group of [ Aspirin ] and Ethanol ( catalyzed by Sulfuric acid ).    

CH3CO-O-(C6H4)-CO-OH [ Aspirin ] + C2H5-OH  ---- >  CH3CO-O-C2H5 [ Ethyl acetate ] + HO-(C6H4)-CO-O-C2H5 [ Ethyl ester of Salicylic acid ]          

Salicylic acid   is  HO-(C6H4)-CO-OH  

Well,  very complicate equations ?