Water → 3-Biphenylylacetic acid

Reaction equation

O.O.[OH-].[Li+].C[O:6][C:7](=[O:21])[CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1>CO>[C:11]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=[C:9]([CH2:8][C:7]([OH:21])=[O:6])[CH:10]=1

Participants

Procedure

Water (39 mL), followed by lithium hydroxide monohydrate (4.2 g, 101.5 mmol) were added to a solution of biphenyl-3-yl acetic acid methyl ester (11.43 g, 50.57 mmol) in methanol (265 mL). The mixture was stirred at ambient temperature for 2h then the organics were removed under reduced pressure. The mixture was acidified with dilute hydrochloric acid (1M, 80 mL), extracted with chloroform (2×100 mL), dried (MgSO4) and evaporated under reduced pressure to afford biphenyl-3-yl acetic acid as a white solid, yield 10.6 g, (99%), analytical HPLC Rt=16.565 min, HPLC-MS (single main UV peak with Rt=7.91 min, 213.1 [M+H]+).