[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Na+].[Cl-]>O1CCCC1.C(OCC)C.O>[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:22][OH:23])=[CH:25][CH:26]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1A suspension of lithium aluminium hydride (309 mg, 7.62 mmol) in anhydrous tetrahydrofuran (65 ml) was added under inert atmosphere with a solution of 4-(4-phenylbutoxy)benzoic acid (1.03 g, 3.81 mmol) in 20 ml of dry ethyl ether. The mixture was left under stirring at room temperature for 2 hours, after that was added slowly with a NaCl saturated solution in water (80 ml), the two phases were separated and the aqueous one was extracted with ethyl acetate (3×50 ml). The organic extracts were dried and the solvent was evaporated off to obtain a crude, which was digested with ethyl ether. The digestion extracts were evaporated under reduced pressure to obtain 556 mg of the title compound (57% yield).
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