Benzyl Bromide → 2-(3-(Benzyloxy)phenyl)ethanol

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:10][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][OH:1])[CH:9]=[CH:8][CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Procedure

To a solution of 3-(2-hydroxyethyl)phenol (1.0 g) and K2CO3 (1.5 g) in acetone (20 mL) was added (bromomethyl)benzene (1.49 g) at ambient temperature. The reaction mixture was stirred at the same temperature for 17 hours. The resulting mixture was evaporated in vacuo. The residue was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=90:10-70:30) to give 2-[3-(benzyloxy)phenyl]ethanol.