Ethylene Glycol → 4-(1,3-Dioxolan-2-yl)benzonitrile

Participants

Reaction Steps

4-Cyanobenzaldehyde (500 mg, 3.81 mmol), ethylene glycol (828 mg, 13.34 mmol) and a catalytic amount of p-toluenesulfonic acid monohydrate were refluxed in toluene (25 mL) overnight in a Dean-Stark apparatus. The reaction mixture was then concentrated and the residue dissolved in chloroform (50 ml) and washed with saturated sodium bicarbonate solution (2×25 mL) and brine (1×25 mL). The organic phase was then dried (Na2SO4) and evaporated to give 4-(1,3-dioxolan-2-yl)benzenecarbonitrile (40) as an oil which solidified to a white solid (633 mg, 95%). 1H NMR (CDCl3, 300 MHz): δ 4.04, t (1.8 Hz), OCH2; 4.07, t (2.0 Hz), OCH2; 5.82, s, H2; 7.64, d (1.4 Hz), 2×ArH; 7.73, d (1.3 Hz), 2×ArH. ESI (+ve) MS: m/z 176 (M+H, 12%).

Provenance & Evidence