Synthesis of acetaminophen

 Category: Acetaminophen

Questions and Answers

What is the function of water in the synthesis of acetaminophen?

it acts as a solvent

What is the stoichiometric reaction for the synthesis of phenacetin from acetaminophen (see image)?

http://img145.imagevenue.com/img.php?image=66753_phenacetin-synthesis_122_723lo.JPG

This is a Williamson Ether Synthesis.

See this image for the reaction.

Thanks!

This is just a simple 2 reactants ---> 1 product reaction. Since you did not specify the quantities, 1 mole of acetominophen should give 1 mole of phenacetin. Usually this reaction is done with an excess of ethyl iodide to make it run a bit faster. Diethyl sulfate works somewhat better but that is extremely toxic.

What is the purpose of water in the synthesis of acetaminophen?

I am trying to figure out exactly what the purpose of the water is in a chem experiment we performed at school. In the reaction water was added to p-aminophenol and acetic anhydride. What purpose did that serve? ie... what exactly does the water do in the reaction.

water hydrolyzes acetic anhydride to promote peptide formation with the primary amine.

What are the pharmacophores of aspirin and acetaminophen (paracetamol)?

I'm a year 12 student in Australia, and I'm really struggling with finding information about the specific chemical structures (including the pharmacophores) and synthesis of aspirin and paracetamol (acetaminophen). I'd really appreicate it if you could answer my question.

http://en.wikipedia.org/wiki/Aspirin

http://en.wikipedia.org/wiki/Paracetamol

I am working on a chemistry lab on williamson ether synthesis. why is ethyl iodide, not ethyl bromide used?

I am studying the conversion of acetaminophen to phenacetin by the williamson ether synthesis. My lab offers the boiling points of both ethyl iodide and ethyl bromide, but when i search for the boiling point of phenacetin, it tells me that no longer exists.

The iodide is a better leaving group than the bromide and plus makes it a more reactive regent to use.

Phenacetin does not have a boiling point because, according to wiki, it decomposes at 134 °C and hence it has a chemical change to its structure.

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