Toluene → 2-Chloromethyl-4,5-dimethoxypyridinium chloride

Participants

Reaction Conditions

Reaction Steps

3 ml of thionyl chloride, dissolved in 10 ml of methylene chloride, are added dropwise to a solution, cooled to 0° C., of 5 g of 2-hydroxymethyl-4,5-dimethoxypyridine in 40 ml of methylene chloride in the course of one hour, the reaction mixture is then stirred at 20° C. for 4 hours, during which it becomes red-colored, 5 ml of toluene are added and the mixture is concentrated completely on a rotary evaporator (30° C./5 mbar). The oily residue is dissolved in 50 ml of warm isopropanol and the solution is clarified with a little Tonsil®, filtered and concentration again. The residue is taken up in 10 ml of toluene and the solution is made to crystallize with petroleum ether. After cooling in an ice-bath, the precipitate is filtered off with suction, washed with petroleum ether and dried. 4.6 g (70% of theory) of the title compound 2-chloromethyl-4,5-dimethoxy-pyridinium chloride are obtained as a colorless solid; decomp. at 160°-161° C.

Provenance & Evidence