Process for preparing (E2,Z6)-2,6-nonadienal
The object of the present invention is to provide an industrial and economical process for preparing (E2,Z6)-2,6-nonadienal of the following formula (4): The present invention provides a process for preparing (E2,Z6)-2,6-nonadienal (4), comprising at least steps of: subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1): to oxidation with a sulfoxide compound of the following formula (2): CH 3 (R 1 )S═O (2) in which R 1 represents a monovalent hydrocarbon group having from 1 to 12 carbon atoms, in the presence of a sulfur trioxide complex and an amine compound of the following formula (3): N(R 2 )(R 3 )(R 4 ) (3) in which R 2 , R 3 , and R 4 each independently represent a monovalent hydrocarbon group having from 1 to 12 carbon atoms, or R 3 and R 4 may be bonded to each other to form a divalent hydrocarbon group having from 3 to 12 carbon atoms, R 3 -R 4 , to form the aforesaid (E2,Z6)-2,6-nonadienal (4).
1. A process for preparing (E2,Z6)-2,6-nonadienal of the following formula (4):
the process comprising at least steps of:
subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1):
to oxidation with a sulfoxide compound of the following formula (2):
CH 3 (R 1 )S═O (2)
in which R 1 represents a monovalent hydrocarbon group having from 1 to 12 carbon atoms,
in the presence of a sulfur trioxide complex and an amine compound of the following formula (3):
N(R 2 )(R 3 )(R 4 ) (3)
in which R 2 , R 3 , and R 4 each independently represent a monovalent hydrocarbon group having from 1 to 12 carbon atoms, or R 3 and R 4 may be bonded to each other to form a divalent hydrocarbon group having from 3 to 12 carbon atoms, R 3 -R 4 ,
to form the aforesaid (E2,Z6)-2,6-nonadienal (4).
2. The process according to claim 1 , wherein the sulfur trioxide complex is selected from the group consisting of a sulfur trioxide pyridine complex, a sulfur trioxide trimethylamine complex, a sulfur trioxide triethylamine complex, a sulfur trioxide ethyldiisopropylamine complex, and a sulfur trioxide N,N-dimethylformamide complex.
3. The process according to claim 1 , wherein the amine compound (3) is selected from the group consisting of a trialkylamine compound and a cyclic tertiary amine compound.
4. The process according to claim 2 , wherein the amine compound (3) is selected from the group consisting of a trialkylamine compound and a cyclic tertiary amine compound.