Water → N-(1-(4-hydroxymethylphenyl)-1-methylethyl)acetamide

Reaction equation

[C:1]([NH:4][C:5]([C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])(=[O:3])[CH3:2].[BH4-].[Li+].O>O1CCCC1>[OH:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([C:5]([NH:4][C:1](=[O:3])[CH3:2])([CH3:7])[CH3:6])=[CH:17][CH:16]=1

Participants

Procedure

To a solution of methyl 4-(1-acetamido-1-methylethyl)benzoate (37.14g) in tetrahydrofuran (370 ml) was added lithium borohydride (6.88 g) and the mixture was refluxed for 19 hr. The reaction mixture was poured into water (1000 ml) and extracted with ethyl acetate (1000 ml). The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from ethyl acetate to give the title compound (18.24 m.p.=126-129° C.