Imidazole → 1-(diethoxymethyl)-1H-imidazole

Participants

Reaction Steps

The procedure of Curtis and Brown was followed: Imidazole (204 g, 3.0M), triethyl orthoformate (1300 ml), and p-toluenesulfonic acid monohydrate (3.0 g) were placed in a 2-liter round bottom with a stirring bar and fitted with a Penn-State distillation head. The reaction was heated at reflux and ethanol removed by distillation. Heating was continued until the reaction temperature rose above 140° C. (ca. 2.5 hours). The reaction was cooled to room temperature and potassium carbonate was added to neutralize the acid catalyst. The desired product was isolated by distillation under vacuum, bp 105° C. (5 mm) after collecting a forerun below 105° C.

Provenance & Evidence