Reaction of a phenol with an aldehyde in the presence of phenylboronic acid gives a 1,3,2-benzodioxaborin. The latter could be reduced to the corresponding ortho-alkylphenol with tert-butylamine borane in the presence of aluminum chloride. Alternatively, the dioxaborin, when reacted with an alkylthiol or an alcohol in the presence of an acid, gave the corresponding ortho-alkylthiomethyl- or ortho-alkoxymethylphenol.
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Lau et al. (1989) studied this question.