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

Participants

Reaction Steps

3-Hydroxy-2-methyl-benzoic acid (1.0 g, 7.2 mmol) in tetrahydrofuran (80 mL) was treated with dropwise added BH3-tetrahydrofuran (1M in tetrahydrofuran) (10 mL). The reaction mixture was stirred at rt overnight. Quenched with 10% NaOH, the mixture was adjusted pH to 7 with 10% HCl and extracted with isopropanol/dichloromethane (1:3) (2×), The organic layers were combined and washed with water, brine, dried to afford the title compound (795 mg, 80%). MS (DCI/NH3) m/z 139 (M+1)+.

Provenance & Evidence