Oxidation of alkoxyphenols. Part XVII. Competitive oxidative demethylation and debromination

Abstract

The action of sodium bismuthate in acetic acid, and of lead tetra-acetate in non-polar solvents, on a series of t-butylphenols with methoxy- and bromo-groups in o- or p-positions has been examined. Quinones, or their precursors, resulting from demethylation rather than debromination, were produced, except in one case, where the bromo-group was ortho to the t-butyl group. Those phenols with an o-methoxy-group gave unstable o-acetoxycyclohexa-2,4-dienone intermediates. The effects of the two oxidants were almost identical.