Cl[C:2]1([CH2:14][CH2:15][CH2:16][C:17]#N)[CH2:7][CH:6]=[CH:5][CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-:19].[K+].[ClH:21].[Cl-].[Na+].[OH2:24]>C(O)CO>[Cl:21][C:7]1[C:2]([CH2:14][CH2:15][CH2:16][C:17]([OH:24])=[O:19])=[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1
A stirred solution of 4-(2-chloro[1,1'-biphenyl]-2-yl)-butanenitrile (2.7 g, 0.011 mole), potassium hydroxide (6.9 g, 0.11 mole), and ethylene glycol (25 ml) in water (25 ml) was heated at reflux for approximately 18 hours. The reaction mixture was cooled to room temperature, diluted with ice water (100 g) and acidified with concentrated hydrochloric acid. The mixture was saturated with sodium chloride, then extracted with diethyl ether (three 100 ml portions) and methylene chloride (100 ml). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to yield 4-(3-chloro[1,1'-biphenyl]-2-yl)butanoic acid as a solid (m.p. 74°-76°).
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