Sodium Hydroxide → (4-Tert-butoxycarbonylphenyl)(hydroxy)phenylacetic acid

Participants

Reaction Steps

To a stirred solution of ethyl(4-tert-butyloxycarbonylphenyl)(hydroxy)phenylacetate from the previous step (78 mg, 0.218 mmol, HPLC RT=2.95 min.) in 2 mL CH3OH was added 0.3 mL of 1 N NaOH solution. Reaction was stirred at room temperature for 4 hours. HPLC analysis indicated rapid conversion to methyl ester but slow saponification to acid. Added 0.1 mL 1 N NaOH to drive reaction to completion. The solvent was removed on a rotary evaporator and the residue was partitioned between EtOAc (20 mL) and 1 N HCl (5 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed on a rotary evaporator. (4-tert-butoxycarbonylphenyl)(hydroxy)phenylacetic acid was obtained as a white solid. (62 mg, 87%); HPLC RT=2.53 min, method B. 1H NMR, 400 MHz, DMSO-d6, 13.4 ppm (br s, 1H); 7.85 ppm (d, J=7.5 Hz, 2H); 7.50 ppm (d, J=7.32 Hz, 2H); 7.34 ppm (m, 5H); and 1.53 ppm (s, 9H).

Provenance & Evidence