Dimethylformamide → 2,2-Dimethyl-3-(4-methoxyphenylmethoxy)propanol

Participants

Reaction Steps

A mixture of 7.7 g (0.32 mole) of sodium hydride and 80 ml of DMF was stirred under an atmosphere of N2 and cooled with an ice-water bath. A solution of 33 g (0.32 mole) of 2,2-dimethylpropandiol in 100 ml of DMF was added dropwise. Stirring was continued until the gas evolution stopped, then a solution of 50 g (0.32 mole) 4-methoxybenzyl chloride was added. The reaction mixture was stirred at room temperature overnight. The resulting solution was poured into an ice-water mixture and the aqueous solution was extracted with ethyl ether three times. The ether solution was washed with H2O, saturated brine, and then dried over MgSO4.

Provenance & Evidence