Dimethylformamide → 3-Benzyloxy-1-propanol

Participants

Reaction Conditions

Reaction Steps

38.05 g(0.50 mol) of propandiol was dissolved in 400 ml of dimethylformamide and cooled to 0° C. 20.0 g(0.5 mol) of 60% sodium hydride dispersed in mineral oil was added slowly. After the mixture was stirred for 10 minutes, 51.31 g(0.30 mol) of benzylbromide dissolved in 100 ml of dimethylformamide was added slowly. After stirring for one hour at room temperature, dimethylformamide was removed under reduced pressure, 500 ml of ethylacetate was added, and the organic layer was washed with saturated sodium chloride solution (200 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to column chromatography to give 33.80 g(0.203 mol, Yield 68%) of the title compound.

Provenance & Evidence