Thionyl Chloride → 3-(Chloromethyl)-2-methylpyridine

Participants

Reaction Steps

To a solution of 3-hydroxymethyl-2-methylpyridine (10.42 g) in toluene (100 ml) was added dropwise thionyl chloride (9.87 ml) at 25° C. After 2.5 hours, the solvent was removed in vacuo to give a residual solid. The solid was dissolved in 4N-aqueous sodium hydroxide (100 ml) and extracted with ethyl acetate. The organic layer was separated, washed with brine and dried over magnesium sulfate. Concentration of the solution gave 3-chloromethyl-2-methylpyridine (9.22 g).

Provenance & Evidence