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A catalytic hypervalent iodine oxidation of p-alkoxyphenols using 4-iodophenoxyacetic acid (1a) and Oxone((R)) was developed. Reaction of p-alkoxyphenol (2) with a catalytic amount of 1a in the presence of Oxone((R)) as a co-oxidant in 2,2,2-trifluoroethanol-water (1 : 2) gave the corresponding p-quinone (3) in excellent yield without special operation. The substituent effect on iodobenzene ring in the oxidation was observed; p-alkoxy is the most effective, with the series following the approximate order p-RO&gt;p-Me, o-MeO, m-MeO&gt;H&gt;o-CO(2)H. And remarkable solvent effects were observed.

Catalytic Hypervalent Iodine Oxidation Using 4-Iodophenoxyacetic Acid and Oxone: Oxidation of p-Alkoxyphenols to p-Benzoquinones