Hydrochloric Acid → 4-Biphenyl-(4'-methoxy)acetic acid

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

Procedure

To a solution of 250 mg (0.93 mmol) of ethyl 4-(4-methoxyphenyl)phenylacetate in 30 ml of ethanol was added, with cooling with ice, 5 ml of 40% sodium hydroxide aqueous solution. This mixture was stirred at room temperature for 2 days. The reaction mixture was neutralized with 3 M hydrochloric acid, and the solvent was then removed by evaporation under reduced pressure. Thereafter, the pH of the resulting mixture was adjusted to 1 with 3 M hydrochloric acid, and this mixture was subjected to extraction with 200 ml of ether. The resulting ether solution was washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, filtered, and then concentrated. Thus, 524 mg (yield 94%) of 4-(4-methoxyphenyl)-phenylacetic acid was obtained.