Chloroform → 4-(2-Benzoyloxyethyl)benzaldehyde

Participants

Reaction Steps

Next, to a mixture of 4-(2-hydroxyethyl)benzaldehyde (6.3 g, 42.2 mmol) and chloroform (170 mL), triethylamine (5.1 g, 50.6 mmol), benzoyl chloride (7.1 g, 50.6 mmol) and 4-dimethylaminopyridine (515 mg, 4.2 mmol) were added at 0° C. The reaction mixture was stirred at room temperature for 2 hours, poured into a mixture of ethyl acetate and water, and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After concentration, the resulting residue was purified by neutral silica gel column chromatography (hexane:ethyl acetate=20:1 to 10:1) to give 4-(2-benzoyloxyethyl)benzaldehyde (5.4 g).

Provenance & Evidence