Benzyl Bromide → 5-(Benzyloxy)-2-methylpyridine

Participants

Reaction Steps

To a solution of sodium ethoxide prepared from 1.3 g. (0.0565 g. -atom) of sodium and 30 ml. of absolute ethanol is added a solution of 5-hydroxy-2-methylpyridine (5.0 g., 0.0458 mol) in 15 ml. of ethanol, followed by 8.6 g. (0.05 mol) of benzyl bromide. The mixture is refluxed for three hours, poured into 150 ml. of water and extracted with ether. The extract is dried and then treated with ethereal hydrogen chloride. The hydrochloride salt is dissolved in water and the aqueous solution is washed with ether, basified and extracted with ether. The dried extract is treated with charcoal and evaporated to give 5-benzyloxy-2-methylpyridine as a pale yellow oil.

Provenance & Evidence