4-Chloro-2-methylbenzoic acid → 4-Chloro-2-methylbenzyl Alcohol

Participants

Reaction Steps

A mixture containing 4-Chloro-2-methyl-benzoic acid (4 g, 23 mmol) and LiAlH4 (890 mg, 23.5 mmol) in 250 mL of THF under a nitrogen atmosphere was allowed to stir at room temperature for 2 hours. The reaction was quenched with sodium sulfate decahydrate. The mixture was filtered through a pad of Celite and the filter cake washed with THF. The filtrate was concentrated under reduced pressure. Purification of the residue via biotage eluting with 30% ethyl acetate/hexanes gave (4-Chloro-2-methyl-phenyl)-methanol (3.70 g, 100%) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 7.30-7.25 (1H, m), 7.18-7.14 (2H, m), 4.66 (2H, d, J 5.8 Hz), 2.32 (3H, s.)

Provenance & Evidence