Cesium carbonate → 2,2,2-Trichloroethyl 4-(4-hydroxymethylphenylacetoxymethyl)-phenylacetate

Participants

Reaction Steps

To a solution of caesium carbonate (1.63 g, 5.00 mmol) in water (50 ml) was added 4-bromomethylphenylacetic acid (12) (1.15 g, 5.00 mmol), and the mixture was refluxed for one hour. After cooling, the reaction mixture was concentrated to dryness under reduced pressure. The residue obtained was suspended in DMF (10 ml). Thereto was added 2,2,2-trichloroethyl 4-bromomethylphenylacetate (13) (1.80 g, 5.00 mmol), and the resulting mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an oil which was purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=15:1) to give 2,2,2-trichloroethyl 4-(4-hydroxymethylphenylacetoxymethyl)phenylacetate (14) as a white solid (994 mg, yield 45%).

Provenance & Evidence