[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4][OH:5].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].BrC1C=CC=CC=1C=O.Cl>C1CCCCC1.CCCCCC>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH:4]=[O:5]
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol (266 mg, 1.2 mmol) was dissolved in cyclohexane (1 mL), added with aluminum isopropoxide (24.5 mg, 0.1 eq, 0.12 mmol) and 2-bromobenzaldehyde (289 mg, 1.3 eq, 1.56 mmol) and stirred at room temperature for 1.5 hours. The reaction mixture was added with hexane, then made acidic with addition of 1 N hydrochloric acid and extracted twice with ethyl acetate. Subsequently, the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 256 mg (yield: 96%, E:Z=99:1) of the title compound as yellow oil.
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