THIELE ACETYLATION OF QUINONES .3. P-BENZOQUINONES WITH BROMO- AND METHOXY-SUBSTITUENTS

The three monobromo-monomethoxy-p-benzoquinones have been prepared; they all undergo Thiele acetylation. The entering acetoxy-group is found ortho or para to the bromine atom in each of the triacetates, and never ortho to the methoxy-group. Thiele acetylation of the three isomeric dibromo-monomethoxy-p- benzoquinones and the three monobromo-dimethoxy-p-benzoquinones has been studied. Of these six compounds the only two which undergo the reaction are 2,6-dibromo-3-methoxy- and 2-bromo-5.6-dimethoxy-p-benzoquinone.