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(z,z,e)-1-chloro-6,10,12-pentadecatriene and method for preparing (z,z,e)-7,11,13-hexadecatrienal by using same

a technology of pentadecatriene and a method of preparing it, which is applied in the field of preparing (z, z, e)7, 11, 13hexadecatrienal, can solve the problems of high yield, high cost, and high risk of reaction, and achieve high reliability and low cost

Active Publication Date: 2014-09-18
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0008]In the invention, it has been found that (Z,Z,E)-1-chloro-6,10,12-pentadecatriene can be mass-produced at a low cost, and (Z,Z,E)-7,11,13-hexadecatrienal can be obtained with high purity and at high yield by converting the (Z,Z,E)-1-chloro-6,10,12-pentadecatriene into a corresponding Grignard reagent, conducting a coupling reaction between the Grignard reagent and ethyl orthoformate, and then conducting a hydrolysis treatment, leading to the completion of the invention.
[0010]According to the invention, none of the steps require an oxidation reaction so that (Z,Z,E)-7,11,13-hexadecatrienal can be mass-produced at a low cost with high reliability.
[0011]Moreover, according to the invention, (Z,Z,E)-7,11,13-hexadecatrienal can be prepared efficiently by coupling the Grignard reagent obtained from (Z,Z,E)-1-chloro-6,10,12-pentadecatriene with ethyl orthoformate.

Problems solved by technology

The oxidation reaction often involves a risk of explosion or the like, and in an industrial scale, it has difficulty in isolating an aldehyde, which is a reaction product, with high purity and high yield.

Method used

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  • (z,z,e)-1-chloro-6,10,12-pentadecatriene and method for preparing (z,z,e)-7,11,13-hexadecatrienal by using same
  • (z,z,e)-1-chloro-6,10,12-pentadecatriene and method for preparing (z,z,e)-7,11,13-hexadecatrienal by using same
  • (z,z,e)-1-chloro-6,10,12-pentadecatriene and method for preparing (z,z,e)-7,11,13-hexadecatrienal by using same

Examples

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Effect test

example 1

Preparation of (Z,Z,E)-1-chloro-3,7,9-dodecatriene (2)

[0043](Z,Z,E)-3,7,9-Dodecatrien-1-ol (169.47 g, 0.94 mol), pyridine (134.2 g, 1.70 mol) and N,N-dimethylformamide (284 g) were placed in a reaction vessel, and stirred at 5 to 10° C. for 30 minutes. After stirring, methanesulfonyl chloride (151.2 g, 1.32 mol) was added dropwise thereto at 5 to 15° C. After completion of the dropwise addition, the reaction mixture was stirred at 60 to 65° C. for 2 hours. Then, water (471 g) was added to the reaction mixture to terminate the reaction. Hexane (471 g) was added thereto to separate the reaction mixture into phases. The organic phase was washed with hydrochloric acid and then with an aqueous sodium bicarbonate solution, and then concentrated by removal of the solvent under reduced pressure. The residue was distilled under reduced pressure to obtain (Z,Z,E)-1-chloro-3,7,9-dodecatriene (bp: 114 to 120° C. / 5 mmHg, 166.93 g, 0.84 mol) with a yield of 89.2%.

[0044][Nuclear magnetic resonance...

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Abstract

Provided are (Z,Z,E)-1-chloro-6,10,12-pentadecatriene that can be synthesized without an oxidation reaction and a method for preparing (Z,Z,E)-7,11,13-hexadecatienal by using (Z,Z,E)-1-chloro-6,10,12-pentadecatriene while not using an oxidation reaction. More specifically, provided is a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal including a step of reacting a Grignard reagent into which (Z,Z,E)-1-chloro-6,10,12-pentadecatriene is converted with ethyl orthoformate to obtain (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene, and a step of treating the (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene with an acid to obtain (Z,Z,E)-7,11,13-hexadecatrienal.

Description

RELATED APPLICATION[0001]This application claims priority from Japanese Patent Application No. 2013-051711, filed Mar. 14, 2013, the disclosure of which is incorporated by reference herein in its entirety.FIELD AND BACKGROUND OF THE INVENTION[0002]The present invention relates to a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal, which is a sex pheromone substance of the citrus leafminer, a pest of citrus, by using (Z,Z,E)-1-chloro-6,10,12-pentadecatriene.[0003]The citrus leafminer (Phyllocnistis citrella) is an important pest of citrus. It is parasitic and causes damage in young leaves and thereby has a serious influence on the growth of nursery trees. Its feeding damage marks accelerate occurrence of citrus canker. This pest mines the undersurface of leaves so that it cannot be controlled easily by pesticides. Its resistance to pesticides is also observed. Biological control methods have therefore been attracting attentions and a method of using a sex pheromone substance is e...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C21/215C07C17/26
CPCC07C17/26C07C21/215C07C41/50C07C45/515C07C17/16C07C17/2632C07C47/21
Inventor MIYAKE, YUKIYAMASHITA, MIYOSHIFUKUMOTO, TAKEHIKOISHIBASHI, NAOKI
Owner SHIN ETSU CHEM IND CO LTD
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