Benzaldehyde, 3,5-dimethyl- → 3-(3,5-Dimethyl-phenyl)-acrylonitrile

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Reaction Steps

To a stirred mixture of 3,5-dimethyl benzaldehyde (13.4 g, 0.1M), diethyl cyanomethylphosphonate (19.4 g, 0.11M) in anhydrous THF (200 ml) under nitrogen at 0° C. (ice bath), was added potassium t-butoxide (12.3 g, 0.11M). After stirring for 1 hr., the mixture was stirred for overnight at room temperature. The mixture was then partitioned between ether and water. The ether layer was taken, dried with anhydrous magnesium sulfate, filtered, evaporated in vacuo, and the residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:20)) to afford 14.8 g (86%) of a white solid. m.p. 67-68° C.; 1H NMR (200 MHz, CDCl3) δ 2.33 (6H, s), 5.83 (1H, d, J=16.6 Hz), 7.05 (3H, s), 7.28 (1H, d, J=16.6 Hz).

Provenance & Evidence