2,6-Dimethylbenzoic acid → (2,6-Dimethylphenyl)methanol

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Reaction Steps

2,6-Dimethylbenzyl alcohol was prepared according to Beaulieu et al. (2000, which is incorporated herein by reference), but was unsuccessful, so a different reducing agent was used. To a suspension of 2,6-dimethylbenzoic acid (1.00 g, 6.65 mmol) in anhydrous THF (10 mL) a solution of BH3(SMe2) in THF was cautiously added under nitrogen atmosphere. The mixture was heated at reflux for 16 hours, then quenched with saturated ammonium chloride (5 mL) and 2 M HCl (10 mL). (CAUTION: vigorous gas evolution!). Organic layer was separated; aqueous layer was extracted three times with ethyl acetate (45 mL each); combined extracts were washed twice with saturated sodium bicarbonate (20 mL each), dried over anhydrous Na2SO4, evaporated, and purified by silica gel chromatography to yield 2,6-dimethylbenzyl alcohol (0.50 g, 51%) as an white solid. 1H NMR (400 MHz, CDCl3): δ 7.08 (m, 3 H, Ph-H), 4.70 (s, 2 H, Ph-CH2), 4.05 (br s, 1 H, OH), 2.40 (s, 6 H, CH3).

Provenance & Evidence