Sodium Hydroxide → m-Chlorophenethylic alcohol

Participants

Reaction Steps

To a mixture of 2-(3-chlorophenyl)acetic acid (11.4 g, 66.7 mmol) in 150 mL of THF was added LiAlH4 (3.04 g, 80.0 mmol) portionwise at 0° C. The resulting mixture was warmed to room temperature and stirred for 2 hours under N2 atmosphere. Then 2 N NaOH (30 mL) was added dropwise and extracted with EtOAc (2×150 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered, and concentrated to provide the crude product which was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=50:1-10:1) to obtain 4.96 g of the title compound as a colorless oil. Yield: 55%.

Provenance & Evidence