Selective reactions using metal phenoxides. Part 2. Reactions with aromatic alcohols

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Abstract
The reactions of aryloxymagnesium bromides (1) with aromatic alcohols in benzene have been studied. In most cases when an ortho-OH group is absent in the alcohol, if any reaction occurs at all it is unselective and gives mixtures of ortho- and para-products. High reactivity and ortho-regioselectivity to give 2,2′-dihydroxydi- and tri-phenylmethanes (3) are achieved with the 2-hydroxybenzyl alcohols (2), especially when the OH group is converted into the magnesium salt. The formation of ortho-quinone methides (7) as intermediates has been postulated to account for the high ortho-regioselectivity observed.

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