Oxidation of Phenols with Iodine in Alkaline Methanol

Article abstract of DOI:10.1021/jo00191a002

The use of iodine as an oxidizing agent for phenolic compounds has been explored.The reaction has been conducted in methanol containing such alkali as potassium hydroxide and, depending on the nature of the substituents and on the amount of iodine employed, leads to iodination, oxidation to give a stable phenoxy radical, oxidative dimerization, or benzylic oxidation.In general the reaction proceeds smoothly at room temperature, and under appropriate conditions yields of products are good to excellent.Oxidative dimerization of 2,4- and 2,6-di-tert-butylphenols invol-ves iodination followed by iodine-catalyzed dimerization.The oxidation of 4-methylphenols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in methanol has been carried out for comparison.