Acetic Acid → 2-(2-Methylbenzylidene)malononitrile

Participants

Reaction Steps

A solution of 2-methylbenzaldehyde (9.6 mL, 83 mmol), malononitrile (5.5 g, 83 mmol) and 3.5 M ammonium acetate in acetic acid (2.4 mL, 8.4 mmol) in isopropanol (83 mL) was stirred overnight at room temperature. A precipitate formed. Water (100 mL) was added and the precipitate was collected. The precipitate was washed with water (50 mL) and vacuum dried to afford of 2-(2-methylbenzylidene)malononitrile (12.7 g) as a white solid (mp 105-106°). 1H-NMR (CDCl3) δ: 8.10 (s 1H); 8.08 (d, 1H); 7.50 (dd, 1H); 7.30-7.40 (m, 2H); 2,45 (s, 3H).

Provenance & Evidence