[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[CH2:9][C:10](O)=[O:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>O1CCCC1.O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
A solution of 25.83 gm (0.10 mol) of 3-(2-fluoro-4-biphenylyl)-butyric acid in 100 ml of absolute tertrahydrofuran was added dropwise at room temperature to a stirred suspension of 2.85 gm (0.075 mol) of lithium aluminum hydride in 100 ml of absolute tetrahydrofuran, the resulting mixture was stirred for 60 minutes more at room temperature and for 30 minutes at 30°-35°C, and then ethyl acetate was added dropwise until no more exothermic reaction occurred. The reaction mixture was then stirred for 15 minutes at room temperature, and thereafter first 50 ml of water and then aqueous 5% hydrochloric acid were added dropwise, accompanied by exterior cooling with ice water, until the precipitate first formed dissolved. The solution was stirred into 2 liters of water, extracted exhaustively with ether, and the combined ether extracts were washed successively with water, saturated aqueous sodium bicarbonate solution and again with water, dried over sodium sulfate, filtered, and evaporated. 18.0 gm (74% of theory) of colorless 3-(2-fluoro-4-biphenylyl)-1-butanol of the formula ##EQU25## which had a melting point of 72°C after recrystallization from cyclohexane.
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