[BH4-].[Na+].[CH2:3]([S:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.Cl>O>[CH2:3]([S:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:17][CH:18]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Sodium 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.
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