Hydrochloric Acid → [4-(Benzylsulfanyl)phenyl]methanol

Participants

Reaction Steps

Sodium borohydride (2.7 g, 67 mmol) was added slowly in three portions to an ice cold mixture of 4-(benzylsulfanyl)-benzaldehyde (7.70 g, 33.7 mmol) and methanol (150 mL). After the addition was complete, the reaction mixture was warmed to room temperature, then stirred for 1 hour. The reaction mixture was cooled again in an ice bath, then 1 N aqueous HCl (80 mL) was added. The resulting mixture was diluted with water (600 mL), then extracted with ethyl acetate (3×250 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. Flash chromatography (Analogix SuperFlash™ column, 5%-50% ethyl acetate in hexanes) gave 6.33 g (81%) of (4-benzylsulfanyl-phenyl)-methanol as a white solid.

Provenance & Evidence