Blankeyblank
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Benzoquinone to Para Benzoquinone
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?
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Nicodem
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I this an April’s fools day question?
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
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Scr0t
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| Quote: | | I recently stumbled on a method to make Benzoquinone from Acetaminophen using DH2O and NaOH and it produces a very brown/black goo.
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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.
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