[CH2:1](O)[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH:9]=[CH:10]\[CH2:11][CH3:12].N1C=CC=CC=1.CN(C)C=O.CS([Cl:29])(=O)=O>CCCCCC.O>[Cl:29][CH2:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH:9]=[CH:10]\[CH2:11][CH3:12](Z,Z,E)-3,7,9-Dodecatrien-1-ol (169.47 g, 0.94 mol), pyridine (134.2 g, 1.70 mol) and N,N-dimethylformamide (284 g) were placed in a reaction vessel, and stirred at 5 to 10° C. for 30 minutes. After stirring, methanesulfonyl chloride (151.2 g, 1.32 mol) was added dropwise thereto at 5 to 15° C. After completion of the dropwise addition, the reaction mixture was stirred at 60 to 65° C. for 2 hours. Then, water (471 g) was added to the reaction mixture to terminate the reaction. Hexane (471 g) was added thereto to separate the reaction mixture into phases. The organic phase was washed with hydrochloric acid and then with an aqueous sodium bicarbonate solution, and then concentrated by removal of the solvent under reduced pressure. The residue was distilled under reduced pressure to obtain (Z,Z,E)-1-chloro-3,7,9-dodecatriene (bp: 114 to 120° C./5 mmHg, 166.93 g, 0.84 mol) with a yield of 89.2%.
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