1-halo-6,9-pentadecadiene and method for producing (7Z,10Z)-7,10-hexadecadienal
AssigneeShin-Etsu Chemical Co., Ltd.
InventorsYuki Miyake, Takeshi Kinsho, Tatsuya Fujii
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Abstract
Provided are a 1-halo-6,9-pentadecadiene useful as an intermediate having a skipped diene skeleton and a method for producing (7Z,10Z)-7,10-hexadecadienal. More specifically, provided are a method for producing (7Z,10Z)-7,10-hexadecadienal including steps of subjecting a Grignard reagent formed from a (6Z,9Z)-1-halo-6,9-pentadecadiene to a nucleophilic substitution reaction with an orthoformate ester to obtain a (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene; and hydrolyzing the (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene in the absence of an oxidation reaction to obtain the (7Z,10Z)-7,10-hexadecadienal; and the like.
Claims6
A method for producing (7Z,10Z)-7,10-hexadecadienal of Formula (9):
- comprising steps of:
- subjecting a Grignard reagent formed from a (6Z,9Z)-1-halo-6,9-pentadecadiene of Formula (1-6Z9Z):
- wherein X stands for a halogen atom,
- to a nucleophilic substitution reaction with an orthoformate ester of Formula (2):
- wherein R may be same with or different from each other and stands for an alkyl group having from 1 to 6 carbon atoms,
- to obtain a (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene of Formula (3):
- wherein R may be same with or different from each other and stands for an alkyl group having from 1 to 6 carbon atoms;
- and
- hydrolyzing the (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene (3) to obtain the (7Z,10Z)-7,10-hexadecadienal (9).
A 1-halo-6,9-pentadecadiene of Formula (1):
- CH3(CH2)4CH═CHCH2CH═CH(CH2)5X (1),
- wherein X stands for a halogen atom.
A method for producing a (6Z,9Z)-1-halo-6,9-pentadecadiene of Formula (1-6Z9Z):
- comprising a step of subjecting a triarylphosphonium (3Z)-3-nonylide of Formula (4-3Z):
- wherein Ar may be same with or different from each other and stands for an aryl group,
- to a Wittig reaction with a 6-halohexanal of Formula (5):
- OHC(CH2)5X (5),
- wherein X stands for a halogen atom,
- to obtain the (6Z,9Z)-1-halo-6,9-pentadecadiene (1-6Z9Z).
Dependencies are inferred from the claim text.