4-Phenylbutyric Acid → 4-Phenylbutanal

Participants

Reaction Steps

A solution of 4-phenylbutyric acid (1.64 g, 10.0 mmol), N,O-dimethyl hydroxylamine hydrochloride (1.58 g, 16 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.06 g, 10.7 mmol), 1-hydroxybenzotriazole (1.56 g, 11.6 mmol), and N-methylmorpholine (2.8 mL, 26 mmol) in dichloromethane (40 mL) at room temperature was stirred for 16 hours, diluted with dichloromethane, washed sequentially with aqueous NaHCO3, brine, 10% KHSO4, and brine, dried (MgSO4), filtered, and concentrated. The concentrate and lithium aluminum hydride (9.0 mmol, 1 equivalent) in diethyl ether (49 mL) at room temperature was stirred 90 minutes, treated with 1M NaHSO4, diluted with ether, washed sequentially with 10% KHSO4, and brine, dried (MgSO4), filtered then concentrated to provide the desired product.

Provenance & Evidence