Hydrochloric Acid → 2-Cyano-4-biphenylcarboxylic acid

Participants

Reaction Steps

To methyl 2-cyano-4-biphenylcarboxylate (D26) (935 mg, 3.94 mmol) was added ethanol (18 ml) but dissolution did not occur so dichloromethane (10 ml) was added. Sodium hydroxide (2 ml, 4.00 mmol) was then added and the reaction stirred for 2 h. To the mixture was added dichloromethane (20 mL) and 2M aqueous HCl (10 mL). The layers were separated and the aqueous extracted with further dichloromethane (20 mL). The combined organic phase was dried (phase separator) and the solvent removed in vacuo to give a white solid, which was dissolved in methanol (30 mL) and aqueous sodium hydroxide was added (2M, 3 mL). The reaction was stirred at room temperature for 1 h before addition of water (20 mL). The reaction was stirred for a further 1 h. Dichloromethane (60 mL) was added and the mixture shaken and the layers separated. The aqueous phase was extracted with further dichloromethane (50 mL) before the combined organic phase was dried (phase separator) and the solvent removed in vacuo to give the title compound as a white solid, (849 mg, 3.80 mmol). δH (d6-DMSO, 400 MHz): 13.60 (1H, br s), 8.38 (1H, d), 8.28 (1H, dd), 7.78 (1H, d), 7.63 (2H, m), 7.60-7.50 (3H, m). MS (ES): C14H9NO2 requires 223; found 222 (M−H+).

Provenance & Evidence