Ethylene Glycol → HCID 11159613, compound

Participants

Reaction Steps

To a solution of 3-formyl-benzonitrile (2 g, 15.25 mmol, 1 eq) in dry toluene (30 mL), paratoluenesulfonic acid (262 mg, 1.5 mmol, 0.1 eq) and ethylene glycol (12.8 mL, 228 mmol, 15 eq) were added and the mixture was heated to reflux in a Dean-Stark apparatus overnight. The toluene was concentrated and the reaction mixture purified by flash chromatography (EtOAc/cHex) to afford the title compound as a colorless liquid (2000 mg, 74%). 1H NMR: (CDCl3, 300 MHz) δ 7.78 (m, 1H), 7.69 (m, 1H), 7.64 (m, 1H), 7.48 (t, J=7.7 Hz, 1H), 5.81 (s, 1H), 4.08 (m, 4H). HPLC (Method A) Rt: 2.45 min (purity: 92.1%).

Provenance & Evidence