Oxidation products of these phenols with metal ions vary with the acidity of the solution, the formation of dimers and trimers in alkaline solution giving place to oxidative demethylation as the acidity is increased. Lead tetra-acetate in acetic acid converts the phenols to mixtures of o-and p-quinones, and in benzene to unstable diacetoxycyclohexadienones. The structures of the monoacetates obtained on hydrogenolysis of the diacetates are proved. Oxidation of 4-methoxy-2-t-butylphenol with benzoyl peroxide leads to an unrearranged catechol monobenzoate, while traces of demethylated products are obtained from 4-methoxy-3-t-butylphenol.
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