Haloalkyl alkoxymethyl ether compound, and process for preparing 4,6,8,10,16-pentamethyldocosane therefrom and for preparing synthetic intermediate therefor

A process for preparing 4,6,8,10,16-pentamethyldocosane of the following general formula (11):

• the process comprising the steps of
• converting a haloalkyl alkoxymethyl ether compound of the following general formula (1:
• n=3):
• 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, 8-alkoxymethoxy-1,3,5-trimethyloctyl compound, of the following general formula (2:
• n=3):
• wherein M1 represents Li, MgZ1, CuZ1, or CuLiZ1, Z1 represents a halogen atom or a 8-alkoxymethoxy-1,3,5-trimethyloctyl group, and R1 is as defined above,
• subsequently subjecting the nucleophilic reagent, 8-alkoxymethoxy-1,3,5-trimethyloctyl compound (2:
• n=3), to a coupling reaction with a 1-halo-2-methylpentane compound of the following general formula (5):
• wherein X2 represents a halogen atom,
• to obtain a 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound of the following general formula (6):
• wherein R1 is as defined above;
• subjecting the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) to a dealkoxymethylation reaction to obtain 4,6,8,10-tetramethyltridecanol of the following formula (7):
• subjecting the 4,6,8,10-tetramethyltridecanol (7) to a halogenation reaction to obtain a 1-halo-4,6,8,10-tetramethyltridecane compound of the following general formula (8):
• wherein X3 represents a halogen atom;
• converting the aforesaid 1-halo-4,6,8,10-tetramethyltridecane compound (8) into a nucleophilic reagent, 4,6,8,10-tetramethyltridecyl compound, of the following general formula (9):
• wherein M2 represents Li, MgZ1, CuZ1, or CuLiZ1, and Z1 represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group,
• and subsequently subjecting the nucleophilic reagent, 4,6,8,10-tetramethyltridecyl compound (9), to a coupling reaction with a 1-halo-3-methylnonane compound of the following general formula (10):
• wherein X4 represents a halogen atom,
• to form the aforesaid 4,6,8,10,16-pentamethyldocosane (11).

A process for preparing 4,6,8,10,16-pentamethyldocosane of the following general formula

• (11)
• the process comprising the steps of
• converting a haloalkyl alkoxymethyl ether compound of the following general formula (1′):
• wherein X1 represents a halogen atom, R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and n represents 2,
• into a nucleophilic reagent, 8-alkoxymethoxy-1,3,5-trimethyloctyl compound, of the following general formula (2:
• n=3):
• wherein M1 represents Li, MgZ1, CuZ1, or CuLiZ1, Z1 represents a halogen atom or a 8-alkoxymethoxy-1,3,5-trimethyloctyl group, and R1 is as defined above,
• subsequently subjecting the nucleophilic reagent, 8-alkoxymethoxy-1,3,5-trimethyloctyl compound (2:
• n=3), to a coupling reaction with a 1-halo-2-methylpentane compound of the following general formula (5):
• wherein X2 represents a halogen atom,
• to obtain a 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound of the following general formula (6):
• wherein R1 is as defined above;
• subjecting the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) to a dealkoxymethylation reaction to obtain 4,6,8,10-tetramethyltridecanol of the following formula (7):
• subjecting the 4,6,8,10-tetramethyltridecanol (7) to a halogenation reaction to obtain a 1-halo-4,6,8,10-tetramethyltridecane compound (8) of the following general formula (8):
• wherein X3 represents a halogen atom;
• converting the aforesaid 1-halo-4,6,8,10-tetramethyltridecane compound (8) into a nucleophilic reagent, 4,6,8,10-tetramethyltridecyl compound, of the following general formula (9):
• wherein M2 represents Li, MgZ1, CuZ1, or CuLiZ1, and Z1 represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group,
• and subsequently subjecting the nucleophilic reagent, 4,6,8,10-tetramethyltridecyl compound (9), to a coupling reaction with a 1-halo-3-methylnonane compound of the following general formula (10):
• wherein X4 represents a halogen atom,
• to form the aforesaid 4,6,8,10,16-pentamethyldocosane (11).