Chloromethyl Methyl Ether → 1-(Methoxymethyl)-4,5-dimethylimidazole

Participants

Reaction Steps

At a temperature of 60° C., 500 mg. of picrinic acid and 15.6 g. (0.39 mol) of sodium hydroxide were added to a solution of 31 g. (0.32 mol) of 4,5-dimethylimidazole (H, Bredereck and G. Theilig, Chem. Ber. 86, 88 (1953)) in 150 ml. of acetonitrile. Then 29 g. (0.36 mol) of chloromethoxymethane were added drop-wise, which made the temperature rise to 80° C. The reaction mixture was refluxed for 6 hours and filtered. The filtrate was concentrated by distilling off the solvent and the residue was distilled. 1-(Methoxymethyl)-4,5-dimethylimidazole was obtained. Boiling point 80°-100° C./1.0 mm. Hg. Melting point of the hydrogen oxalate 102°-103° C.

Provenance & Evidence