Hydrochloric Acid → Ethyl 3-methoxy-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

Participants

Reaction Steps

Trifluoromethanesulfonic anhydride (0.944 mL) was added to an ice-cooled mixture of ethyl vanillate (1.00 g) and pyridine (0.454 mL) in methylene chloride (5 mL) with stirring, and the mixture was stirred for 10 minutes. The reaction mixture was poured into a mixture of 1 mol/L hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10) to afford ethyl 3-methoxy-4-trifluoromethanesulfonyloxybenzoate (1.467 g).

Provenance & Evidence