3-Hydroxy-2-methylbenzoic Acid → 3-(Hydroxymethyl)-2-methylphenol

Participants

Reaction Steps

Borane-tetrahydrofuran (1M in THF, 4.6 mL, 1.4 eq) was added to a solution of 2-methyl-3-hydroxybenzoic acid (0.50 g, 3.3 mmol) in THF (30 mL). The reaction mixture was stirred overnight at rt before addition of saturated sodium hydrogencarbonate. The aqueous phase was extracted with DCM. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford 3-(hydroxymethyl)-2-methylphenol in a quantitative yield.

Provenance & Evidence