Sodium borohydride → 2-(3-Nitrophenyl)propan-1-ol

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[CH:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+]>C(O)C.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Procedure

In ethanol (100 ml) was dissolved 7.531 g of 2-(3-nitrophenyl)propanal. Under ice-cooling, sodium borohydride (1.9 g) was added thereto, followed by stirring at room temperature for 1 hour. To the mixture was added brine, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The resulting residue was purified by silica gel column, to give the title compound (6.275 g, 57.19% in 3 steps) as a brown oil.