m,alpha-Dichlorotoluene → 5-(m-Chlorobenzyloxy)-2-pyridinemethanol

Participants

Reaction Steps

The solution of 16.2 g of 5-hydroxy-2-pyridinemethanol hydrochloride in 150 ml of methanol is added to a solution of 4.6 g of sodium in 250 ml of methanol, while stirring, over a period of 25 minutes. The solution is stirred for one hour and then a solution of 19.3 g of m-chlorobenzyl chloride in 50 ml of methanol is added. Then the mixture is refluxed for 19 hours, cooled, filtered and the filtrate evaporated to a residue. The residue is suspended in 100 ml of water, made basic with 20% aqueous sodium hydroxide solution and then extracted with chloroform. The chloroform extract is separated, dried over sodium sulfate, filtered and the filtrate evaporated, to yield 5-(m-chlorobenzyloxy)-2-pyridinemethanol melting at 78°-80°.

Provenance & Evidence