Pyridine → 1-(Benzyloxy)-2-(chloromethyl)benzene

Participants

Reaction Steps

To a solution of 46.5 (0.217 mole) 2-benzyloxybenzyl alcohol (prepared by reaction of 2-hydroxybenzyl alcohol with benzyl chloride in ethanol containing an equimolar amount of potassium t-butoxide at 100° C.) in 100 ml chloroform was added 17.2 g (0.217 mole) pyridine followed by dropwise addition of a solution of 25.8 g (0.217 mole) thionyl chloride in 60 ml chloroform. The resulting mixture was heated at reflux for 1.5 hours, cooled, washed with water, brine and dried (MgSO4). Evaporation of solvent gave 45.8 g crude oil which was distilled in vacuo to yield 40.7 g (81%) of product as a colorless oil, b.p. 141° C.(1 Torr).

Provenance & Evidence