[C:1](OCC)(=[O:13])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC(C[AlH]CC(C)C)C.C(OCC)C>CCCCCCC.[Cl-].[Na+].O>[CH2:1]([OH:13])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Under nitrogen atmosphere, (2E,4E)-ethyl dodeca-2,4-dienoate (6.1 g) was dissolved in n-heptane (120 ml) and cooled to −70° C. DIBAL-H in hexanes (82 ml) was added dropwise and the mixture was stirred at −70° C. for 45 min. Brine (60 ml) and diethyl ether (100 ml) were added and the mixture was stirred for 45 min while warming to RT. The organic layer was separated and washed with 1N HCl, dried over sodium sulfate, filtered and concentrated. A colorless liquid was isolated that solidified upon slight cooling.
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