Sciencemadness Discussion Board

Reduction of P-Aminophenol to aniline?

Jackson - 23-4-2019 at 08:23

Could a reduction of p-aminophenol to aniline through the use of zinc dust work? I am looking to synthesize aniline without going through nitrobenzene or benzene, but also with relatively OTC compounds (p-aminophenol could be obtained from acetaminophen). Would a Hoffman rearrangement of benzamide obtained from Benzoic acid be better?

draculic acid69 - 25-4-2019 at 04:44

I wonder if para amino benzoic acid can be reacted like sodium benzoate and NaOH to yeilds aniline?going through benzene and nitrobenzene and a reduction seems tedious.paracetamol has a hydroxy that would be hard to get rid of.but it is super cheap and easy.

Chemi Pharma - 10-5-2019 at 23:37

You can convert phenols to anilines via Smiles rearrangement using Chloroacetamide, KI, K2CO3 and DMF, like said in the paper I attached. So, a better route to your target, since you don't want to use benzene or nitrobenzene, is starting from phenol and convert it into aniline this way. If you start from p-aminophenol you will get p-Phenylenediamine.

You can start from Chlorobenzene, amonea and cooper oxide under heat and pressure to obtain aniline either.

Attachment: phenols to anilines with chloroacetamide, K2CO3, KI and DMF.PDF (1.9MB)
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