[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[BH4-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:7])[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:14][CH:15]=1To a solution of 10.6 g of 4-(4-chlorobenzoyl)butanoic acid and 1.9 g of sodium hydroxide in 50 ml of water was added under ice-cooling 2.7 g of sodium borohydride portionwise over 35 minutes, and the mixture was stirred at room temperature for 24 hours. The mixture was made acidic with diluted hydrochloric acid under ice-cooling, extracted with ether. The ether extract was washed with water and dried. After removal of the solvent, the residue was recrystallized from a mixture of ethyl acetate-n-hexane to give 7.50 g of 5-(4-chlorophenyl)-5-hydroxypentanoic acid as colorless crystals.
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