Acetic Anhydride → (1-Ethoxyethylidene)malononitrile

Participants

Reaction Steps

Into a 250-mL 3-necked round-bottom flask, was placed malononitrile (20.4 g, 309.09 mmol, 1.00 equiv) at room temperature. To the resulting mixture was then added 1,1,1-triethoxyethane (50 g, 308.64 mmol, 1.00 equiv), in portions at room temperature. To the resulting mixture was then added acetic anhydride (72 g, 705.88 mmol, 2.28 equiv), in portions at room temperature. The resulting solution was heated to reflux for 3 hr. The resulting mixture was concentrated under vacuum, then cooled with a water/ice bath. The solids were collected by filtration to yield 2-(1-ethoxyethylidene)malononitrile as a white solid.

Provenance & Evidence