Haloalkenyl alkoxymethyl ether compound and a process for preparing a terminal conjugated alkadien-1-yl acetate compound and a terminal conjugated alkadien-1-ol compound therefrom

A process for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5):

• CH2═CHCH═CH(CH2)aOAc (5)
• wherein “a” represents an integer of 3 to 14, and Ac represents an acetyl group, the process comprising:
• dealkoxymethylating a haloalkenyl alkoxymethyl ether compound of the following general formula (1):
• R1CH2OCH2OCH2CH2CH═CH(CH2)aX1 (1)
• wherein R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X1 represents a halogen atom, and “a” is as defined above
• to prepare a halo-3-alken-1-ol compound of the following general formula (2):
• HOCH2CH2CH═CH(CH2)aX1 (2)
• wherein X1 and “a” are as defined above;
• acetoxylating the halo-3-alken-1-ol compound (2) to prepare a hydroxyalkenyl acetate compound of the following general formula (3):
• HOCH2CH2CH═CH(CH2)aOAc (3)
• wherein “a” and Ac are as defined above;
• halogenating the hydroxyalkenyl acetate compound (3) to prepare a haloalkenyl acetate compound of the following general formula (4):
• X2CH2CH2CH═CH(CH2)aOAc (4)
• wherein X2 represents a halogen atom, and “a” and Ac are as defined above;
• and
• subjecting the haloalkenyl acetate compound (4) to an elimination reaction in the presence of a base to prepare the terminal conjugated alkadien-1-yl acetate compound (5).