Easy synthesis of 2,4-dialkyl substituted phenols and anisoles from p-benzoquinone

Article abstract of DOI:10.1016/S0040-4020(01)88530-6

The reaction of p-benzoquinone (1) with several organolithium compounds (methyl-, ethyl-, n-butyl, phenyllithium) leads directly, after acid hydrolysis, to the corresponding 2,4-dialkylphenols 4a-d, resulting from a rearrangement/aromatization process of the corresponding intermediate diols 3. The use of two different alkyllithium reagents leads to the mixed products 4e f. Alternatively, the same results are obtained treating the crude isolated diols 3 with a catalytic amount of concentrated sulfuric acid. Applying this last methodology to the diethers 2, 2,4-dialkylanisoles 8 are obtained. A possible mechanism is proposed.