On the oxidation of 2-t-Butyl-p-cresol

Abstract

While oxidation of alkaline solutions of 2-t-butyl-p-cresol by ferricyanide or silver oxide gives the ortho-para-coupled Pummerer's ketone (6), ferric chloride in slightly acid solution gives the ortho- coupled biphenyldiol (5). With ddq in methanol the cresol is further oxidized, again through ortho coupling, to the lactone (10), in which one of the aromatic rings has been cleaved, and to the dibenzo-furan (9). Minor products, both monomeric and dimeric, in which the methyl group has been oxidized via the quinone methide, were also identified.