Oxidation of alkoxyphenols. Part XV. Autoxidation of 2- and 3-mono- and 2,5-di-t-butyl-4-methoxyphenol and related compounds

Abstract

Autoxidation of 4-methoxy-2-t-butylphenol gives the ortho-coupled diol, which, in turn, is autoxidised to 8-methoxy-2,6-di-t-butyldibenzofuran-1,4-quinone. Autoxidation of 4-methoxy-3-t-butylphenol also gives some diol, but the major product is 3-hydroxy-2-(4-methoxy-3-t-butylphenoxy)-5-t-butyl-1,4-benzoquinone. Autoxidation of 4-methoxy-2,5-di-t-butylphenol gives a mixture from which 2,5-di-t-butyl-1,4-benzoquinone, its monoepoxide, and the cis- and trans-diepoxides were isolated. The reactions of these epoxides with various reducing agents and with hydrogen halides are described, and confirm the assigned structures.