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

Participants

Reaction Steps

A solution of 4-formylbenzonitrile (10 g, 76.3 mmol), ethylene glycol (18.95 g, 305 mmol) and p-toluene sulfonic acid (7 mg, 0.003 mmol) in toluene (100 mL) was heated to reflux for 9 hours. During this time a Dean-Stark trap was used to remove water formed during the reaction. To the reaction was added aq. Na2CO3 (150 mL). The organic layer was washed twice with water (100 mL), then dried over Na2SO4. The solvent was removed under vacuum to provide 4-(1,3-dioxolan-2-yl)benzonitrile (12 g, 68 mmol). The compound had an HPLC retention time=4.24 min. −Column: HYPERSIL® BDS C18 (4.6×50 mm) Flow rate=0.8 mL/min. Solvent A=, 0.1% TFA in water; Solvent B=acetonitrile. 5%-100% B (0-6 min), 100% B (6-9 min), 100%-5% B (9-11 min).

Provenance & Evidence