Water → 3-Biphenylylacetic acid

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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

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실험 절차

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 2 h 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]+).