Sciencemadness Discussion Board

Benzoquinone to Para Benzoquinone

Blankeyblank - 1-4-2015 at 21:49

Hi I have been synthesizing P Benzo from Hydroquinone for a while now with a slightly modified version of an Erowid method involving H202 and Iodine as a catalyst https://erowid.org/archive/rhodium/chemistry/benzoquinone.ht... but I recently stumbled on a method to make Benzoquinone from Acetaminophen using DH2O and NaOH and it produces a very brown/black goo. Is there anyway the Benzo produced from Acetaminophen can be used in place of Hydroquinone?

Nicodem - 2-4-2015 at 08:00

I this an April’s fools day question?

Scr0t - 2-4-2015 at 10:39

Quote:
I recently stumbled on a method to make Benzoquinone from Acetaminophen using DH2O and NaOH and it produces a very brown/black goo.

Do you have a reference for this? What you describe just sounds like a base hydrolysis of paracetamol to p-aminophenol which would be very susceptible to atmospheric oxidation under basic conditions to give the dark colour that you describe. Acid hydrolysis would be preferable.

p-aminophenol can be oxidized with dichromate to give the benzoquinone...
http://www.orgsyn.org/demo.aspx?prep=cv4p0148


As side note V2O5 catalyzed oxidation of hydroquinone with NaClO3 works well but gives very poor yields of p-benzoquinone if applied to p-aminophenol.


I imagine you want p-benzoquinone for a Benzo-Wacker reaction given your previous post.
Aqua-regia oxidation of paracetamol is effective at making chlorinated benzoquinones although I don't know if they would be useful as an oxidant in this reaction, maybe.