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

Participants

Reaction Steps

4-Formyl-benzonitrile (3.00 g, 22.9 mmol), ethane-1,2-diol (6.38 mL, 115 mmol) and toluene-4-sulfonic acid monohydrate (197 mg, 1.15 mmol) were dissolved in toluene (60 mL), and the solution was stirred under reflux for 10 hours. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=10:1), and the title compound (3.78 g, 21.6 mmol, 94%) was obtained as a white solid.

Provenance & Evidence