Phenol → HCID 573755, compound

Participants

Reaction Steps

Phenol (5.0 g, 39.0 mmol), a 1M solution of 1,3-dicyclohexylcarbodiimide in dichloromethane (39.0 mL, 39.0 mmol) and 4-dimethylaminopyridine (0.5 g, 3.9 mmol) were added to a solution of thiophene-2-carboxylic acid (5.0 g, 39.0 mmol) in diethyl ether (400 mL) at about 0° C. The reaction mixture was stirred overnight while being allowed to warm to room temperature. The precipitate was collected by filtration and was washed with diethyl ether. The combined filtrates were washed successively with water, 5% aqueous acetic acid, water and brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (5:1) as the mobile phase to provide phenyl thiophene-2-carboxylate. MS (DCI-NH3): m/z 222 (M+NH4)+.

Provenance & Evidence