Ethylene Glycol → N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}phthalimide

Participants

Reaction Steps

To a solution of N-[3-(3-formylphenoxy)propyl]phthalimide (92.8 g, 0.3 mole), ethylene glycol (44 mL, 0.8 mole) in benzene (1.5 L) was added 3 g of p-toluenesulfonic acid and the mixture was refluxed under a Dean-Stark trap for 14 hours. The cooled mixture was extracted with 100 mL of saturated aqueous sodium bicarbonate and then with 200 mL of saturated aqueous sodium chloride. The organic phase was dried and evaporated under reduced pressure to give 119.4 g of the title compound which crystallized on standing.

Provenance & Evidence