6-hydroxy-3-hexenyl alkoxymethyl ether compound and a process for preparing a 3,13-octadecadien-1-ol compound from the same

A process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6):

• CH3(CH2)3CH═CH(CH2)8CH═CHCH2CH2OH (6),
• the process comprising:
• halogenating a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1):
• HOCH2CH2CH═CHCH2CH2OCH2OCH2R1 (1)
• wherein R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group
• to prepare a 6-halo-3-hexenyl alkoxymethyl ether compound of the following general formula (2):
• X1CH2CH2CH═CHCH2CH2OCH2OCH2R1 (2)
• wherein X1 represents a halogen atom, and R1 is as defined above;
• converting the 6-halo-3-hexenyl alkoxymethyl ether compound (2) into a nucleophilic reagent, 6-(alkoxymethoxy)-3-hexenyl compound of the following general formula (3):
• MCH2CH2CH═CHCH2CH2OCH2OCH2R1 (3)
• wherein M represents Li, MgZ2, CuZ2, or CuLiZ2, wherein Z2 represents a halogen atom or a 6-(alkoxymethoxy)-3-hexenyl group, and R1 is as defined above;
• subjecting the nucleophilic reagent, 6-(alkoxymethoxy)-3-hexenyl compound (3), to a coupling reaction with a 12-halo-5-dodecene of the following general formula (4):
• CH3(CH2)3CH═CH(CH2)6X2 (4)
• wherein X2 represents a halogen atom,
• to prepare a 3,13-octadecadiene alkoxymethyl ether compound of the following general formula (5):
• CH3(CH2)3CH═CH(CH2)8CH═CHCH2CH2OCH2OCH2R1 (5)
• wherein R1 is as defined above;
• and
• dealkoxymethylating the 3,13-octadecadiene alkoxymethyl ether compound (5) to prepare the 3,13-octadecadien-1-ol compound (6).