5-Nitro-2-(phenylsulfanyl)benzaldehyde → [5-Nitro-2-(phenylsulfanyl)phenyl]methanol

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[BH4-].[Na+]>C(O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][CH:11]=1)[CH2:7][OH:8])([O-:3])=[O:2]

Participants

Procedure

450 g of 3-nitro-6-(phenylthio)-benzaldehyde are suspended in 4 litres of ethanol and treated portionwise with 111 g of sodium borohydride. The mixture is stirred for a further 6 hours. The mixture is then diluted with 4 litres of water and extracted with ether. The organic solution is washed successively with water and aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated under reduced pressure. The crude product is recrystallised from benzene/petroleum ether. There is obtained 3-nitro-6-(phenylthio)-benzyl alcohol of melting point 104°-107° C.