Methanol → 3-(Hydroxymethyl)-2-methylphenol

Participants

Reaction Conditions

Reaction Steps

A solution of 3-hydroxy-2-methylbenzoic acid (44.4 g, 285 mmol) (prepared as described in Preparation 1A) dissolved in dry tetrahydrofuran (200 mL) was added to 1 M borane in tetrahydrofuran (800 mL) while stirring at a temperature of 0° C. The resulting semisolid mixture was heated in a mantle to just short of reflux and heating was maintained for about 15 hours. Methanol (200 mL) was added to the reaction mixture. The resultant clear solution was evaporated in vacuo and then evaporated with further portions of methanol to give 3-hydroxymethyl-2-methylphenol (30.3 g, 99%).

Provenance & Evidence