O.[O:2]1CCCC1.[CH3:7][C:8](/[CH:15]=[CH:16]/[CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[BH4-].[Na+]>[OH-].[Na+]>[OH:2][C:22]([CH3:23])([CH3:24])[CH2:21][CH2:20][CH2:19][CH:18]([CH3:25])[CH2:17][CH:16]=[CH:15][C:8]([CH3:7])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]To a mixture of 1.9 g. of mercuric acetate, 6 ml. of water and 20 ml. of tetrahydrofuran is added 1.49 g. of trans ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate slowly. After addition is complete, the reaction mixture is stirred for about 20 minutes. The mixture is cooled to about 0° and 6 ml. of aqueous sodium hydroxide (3 molar) is added followed by 0.49 g. of sodium borohydride in aqueous sodium hydroxide (about 3 molar). The mixture is stirred for about 30 minutes. The mixture is then decanted, concentrated, diluted with water and then extracted with ether. The ethereal extract is washed with water, dried over magnesium sulfate and the product chromatographed on silica gives ethyl 11-hydroxy-3,7,11-trimethyldodeca-2,4-dienoate (trans).
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