Sciencemadness Discussion Board

Benzoquinones via phenol?

Theophrastus_2 - 11-1-2010 at 16:11

Sorry for the noob question, but if one were to oxidise phenol with a strong excess of Jones reagent (chromic acid), would the products be a mixture of 1,2 and 1,4 benzoquinones?

JohnWW - 11-1-2010 at 16:26

Aniline undergoes oxidation with Cr(VI) to give 1,4-benzoquinone, which is yellow (as is also anthraquinone); but it may take more severe oxidizing conditions to oxidize phenol to that compound. There should not be any 1,2 benzoquinone produced. The usual route to 1,4-benzoquinone is by mild oxidation of 1,4-hydroquinone (para HO-C6H4-OH), with even Fe(III) salts.