Haloalkyl alkoxymethyl ether compound, and process for preparing 13,15-dimethylheptacosane therefrom and for preparing synthetic intermediate therefor

A process for preparing 13,15-dimethylheptacosane of the following general formula (11):

• the process comprising the steps of
• converting a haloalkyl alkoxymethyl ether compound of the following general formula (1B):
• wherein X1 represents a halogen atom, and R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group,
• into a nucleophilic reagent, 6-alkoxymethoxy-1,3-dimethylhexyl, of the following general formula (2B):
• wherein M2B represents Li, MgZ2B, CuZ2B, or CuLiZ2B, Z2B represents a halogen atom or a 6-alkoxymethoxy-1,3-dimethylhexyl group, and R1 is as defined above,
• subsequently subjecting the nucleophilic reagent, 6-alkoxymethoxy-1,3-dimethylhexyl (2B), to a coupling reaction with a 1-halododecane compound of the following general formula (5):
• X2(CH2)11CH3 (5)
• wherein X2 represents a halogen atom,
• to obtain a 4,6-dimethyloctadecyl alkoxymethyl ether compound of the following general formula (6):
• wherein R1 is as defined above,
• subjecting the 4,6-dimethyloctadecyl alkoxymethyl ether compound (6) to a dealkoxymethylation reaction to obtain 4,6-dimethyloctadecanol of the following formula (7):
• subjecting the 4,6-dimethyloctadecanol (7) to a halogenation reaction to obtain a 1-halo-4,6-dimethyloctadecane compound of the following general formula (8):
• wherein X3 represents a halogen atom,
• converting the 1-halo-4,6-dimethyloctadecane compound (8) into a nucleophilic reagent, 4,6-dimethyloctadecyl, of the following general formula (9):
• wherein M2 represents Li, MgZ2, CuZ2, or CuLiZ2, and Z2 represents a halogen atom or a 4,6-dimethyloctadecyl group,
• and subsequently subjecting the nucleophilic reagent, 4,6-dimethyloctadecyl (9), to a coupling reaction with a 1-halononane compound of the following general formula (10):
• X4(CH2)8CH3 (10)
• wherein X4 represents a halogen atom,
• to form the aforesaid 13,15-dimethylheptacosane (11).