Water → 5-(Benzyloxy)pentan-1-ol

Participants

Reaction Conditions

Reaction Steps

31.5 g of sodium hydride (60%) is introduced at room temperature in portions in 900 ml of absolute DMF. 104.8 ml of 1,5-pentanediol in 450 ml of absolute DMF is added in drops to the suspension that is cooled to −20° C. in such a way that the internal temperature does not exceed −15° C. After the addition has been completed, a solution of 121 ml of benzyl bromide in 870 ml of absolute DMF is quickly added in drops, and then the reaction mixture is stirred for 30 minutes at room temperature. The reaction is completed by careful addition of 315 ml of water. For working-up, the reaction mixture is stirred into 1.5 l of water and extracted 3 times with 1 l of ether in each case. The ethereal phases are combined, washed with water, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography on silica gel with a hexane-ethyl acetate gradient yields 85 g of 5-benzyloxy-pentan-1-ol as an oil.

Provenance & Evidence