Benzyl Chloride → 2,5-Dimethyl-4-(phenylmethoxy)benzenemethanol

Participants

Reaction Steps

A mixture of 18.0 g (118 mmol) of 4-hydroxy-2,5-dimethyl-benzenemethanol (Example H), 14.9 g (118 mmol) of benzyl chloride and 18.0 g (1.1×118 mmol) of anhydrous potassium carbonate in 300 mL of acetonitrile is stirred at reflux for 18 hours overnight. The reaction flask and inorganic residue are washed with fresh acetonitrile and the solvent is removed on a rotary evaporator. A diethyl ether solution of the residue is washed with 2×50 mL of 2N potassium hydroxide solution, brine, dried (magnesium sulfate) and evaporated leaving 28.3 g of a pale yellow viscous residue. Distillation through a short path apparatus affords the title compound; mp 58°-59° C.

Provenance & Evidence