Ethylene Glycol → N-methyl-N-(1,3-dioxolan-2-ylmethyl)-alpha-chloroacetamide

Participants

Reaction Steps

N-Methyl-N-(2,2-dimethoxyethyl)-α-chloroacetamide (19.5 grams; 0.10 mole), ethylene glycol (6.82 grams; 0.11 mole) and 10 drops of a solution of toluene sulfonic acid (1 gram) in ether (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and distillation head. The mixture was heated at 100° to 110° C. with stirring and the methanol removed as it was formed. After no more methanol was given off the reaction mixture was cooled to room temperature and was stirred with about 2 grams of sodium carbonate for a period of about 1 hour. After this time the reaction mixture was filtered and the filtrate was distilled under reduced pressure to yield the desired product N-methyl-N-(1,3-dioxolan-2-ylmethyl)-α-chloroacetamide having a boiling point of 119° to 124° C. at a pressure of 0.15 to 0.30 mm of Hg.

Provenance & Evidence