Sciencemadness Discussion Board

p-Aminophenol to Phenol

TheChemiKid - 25-1-2014 at 09:50

Is there any way to synthesize phenol or other Benzene-related compounds (Aniline, Nitrobenzene, Benzene) from p-Aminophenol?

UnintentionalChaos - 25-1-2014 at 10:06

Short answer: No.

Long answer: Yes, but the methods are most likely beyond the means of most amateurs (and far from cost effective or worth the effort). A diazonium salt prepared from p-aminophenol could be reduced by hypophosphorous acid to phenol. I suggest the approach through salicylic acid instead for cost effectiveness (plus aspirin feedstock is cheaper than acetaminophen).

Distillation of p-aminophenol over zinc dust might be able to produce aniline (and aniline can be oxidized to nitrobenzene using extremely strong oxidants (I think oxone and permanganate can be made to work in certain conditions).

Both benzene and nitrobenzene are much easier to get to from the sodium benzoate/NaOH distillation discussed elsewhere on this forum and mild nitration of the resulting benzene. Reduction of nitrobenzene to aniline is a well documented and simple reaction, whereas zinc dust distillation has probably not been used appreciably in most of a century.

TheChemiKid - 25-1-2014 at 10:13

Thank you for the help. I will try distilling over zinc dust in a while, and will get back when I have finished. Unfortunately, I don't have zinc dust on hand.
Can I precipitate zinc from solution to make a fine enough dust?

EDIT: Would you mind saying more on the salicylic acid method?

[Edited on 1-25-2014 by TheChemiKid]

UnintentionalChaos - 25-1-2014 at 10:40

I mean this in the nicest way possible, but UTFSE. It's on this forum. Reference hunting is one of the most valuable skills you can develop.