Acetic Acid → 2-Amino-alpha-methylbenzenemethanol

Participants

Reaction Steps

Sodium borohydride (1.12 g, 29.6 mmol) was stirred under nitrogen in THF (40 mL) in an ice bath. Acetic acid (3.38 mL, 3.55 g, 59.2 mmol) was added dropwise. The mixture was stirred until hydrogen evolution had ceased, then neat 2-aminoacetophenone (2.0 g, 14.8 mmol) was added dropwise. The mixture was stirred at ambient temperature for 5 days, then treated with water (40 mL) and neutralized with saturated aqueous sodium bicarbonate. The mixture was extracted with ether, and the combined ether layers were dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give methyl-2-aminophenyl carbinol.

Provenance & Evidence