ortho-Specific alkylation of phenols via 1, 3, 2-benzodioxaborins

…, C Dufresne, J Scheigetz, PC Bélanger

Index: Lau, Cheuk K.; Williams, Haydn W. R.; Tardiff, Sylvie; Dufresne, Claude; Scheigetz, John; Belanger, Patrice C. Canadian Journal of Chemistry, 1989 , vol. 67, p. 1384 - 1387

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Citation Number: 21

Abstract

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. Key words: phenol, ...