[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[C:12]1([CH:18]([CH2:23][C:24](O)=[O:25])[CH2:19][C:20](O)=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>O1CCCC1>[C:12]1([CH:18]([CH2:19][CH2:20][OH:21])[CH2:23][CH2:24][OH:25])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1To a suspension of 9.10 g (240 mM) of lithium aluminum hydride in tetrahydrofuran (500 ml)-diethyl ether (200 ml) was added a solution of 24.960 g (119.9 mM) of 3-phenylglutaric acid in 100 ml of tetrahydrofuran dropwise with ice-cooling and the mixture was stirred at room temperature overnight. To this reaction mixture was added water gradually dropwise under ice-cooling until a precipitate had formed. The precipitate was filtered off with the aid of celite and washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure to provide crude 3-phenylpentane-1,5-diol. This crude product was not purified but used as it was in the next reaction. (Brown liquid, yield 19.19 g).
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