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Synthetic method for (Z/E)-8-dodecylene-1-ol acetate compound

A technology of dodecene and alcohol acetate, applied in the field of pesticides, can solve problems such as unfavorable large-scale production, difficult post-processing, many side reactions and the like

Active Publication Date: 2015-05-06
SHANDONG ACADEMY OF PESTICIDE SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, it is not suitable for low-temperature reaction, and there are many side reactions, resulting in many impurities in the product, difficult post-processing, and unfavorable for large-scale production.

Method used

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  • Synthetic method for (Z/E)-8-dodecylene-1-ol acetate compound
  • Synthetic method for (Z/E)-8-dodecylene-1-ol acetate compound
  • Synthetic method for (Z/E)-8-dodecylene-1-ol acetate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Synthesis of ω-bromooctyltriphenylphosphonium bromide salt

[0031] Put 13.50 (50 mmol) of 1,8-dibromooctane and 13.10 (50 mmol) of triphenylphosphine into 150 ml of benzene, heat and reflux for 20 hours, after the reaction is completed, pour out the benzene layer, remove the remaining benzene, and obtain ω-bromo Substituent octyltriphenylphosphonium bromide salt 23.10g, yield 86.9%.

[0032] (2) Synthesis of ω-bromododecene

[0033] Under the protection of nitrogen, 22.30g (40mmol) ω-bromoquaternary phosphine salt was added to the mixed solvent (25ml tetrahydrofuran and 5ml diglyme), stirred and dissolved while maintaining the temperature at 20°C, slowly added 24ml2. 5mol / L tetrahydrofuran solution of dimethyl sulfoxide sodium salt, stirred for 1h, then cooled to -15°C, added n-butyraldehyde, kept warm for 10h, followed by TLC detection, added ice water after the reaction of raw materials, adjusted with 10% hydrochloric acid Neutral pH, extracted with ether, comb...

Embodiment 2

[0039] (1) Synthesis of ω-bromooctyltriphenylphosphonium bromide salt

[0040] Put 13.50 (50 mmol) of 1,8-dibromooctane and 14.41 (55 mmol) of triphenylphosphine into 150 ml of benzene, heat and reflux for 18 hours, after the reaction is completed, pour out the benzene layer, remove the remaining benzene, and obtain ω-bromo Substituent octyltriphenylphosphonium bromide salt 23.10g, yield 87.50%.

[0041] (2) Synthesis of ω-bromododecene

[0042]Under the protection of nitrogen, add 26.60g (50mmol) ω-bromoquaternary phosphonium salt into the mixture of 25ml tetrahydrofuran and 5ml diethylene glycol dimethyl ether, stir to dissolve and maintain the temperature at 20°C-30°C, slowly add 25ml2 .5mol / L tetrahydrofuran solution of dimethyl sulfoxide sodium salt, stirred for 1 hour, then cooled to -20°C, added n-butyraldehyde, kept for 13 hours, followed by TLC detection. Adjust the pH to be neutral, extract with ether, combine the organic phases, wash with saturated aqueous sodium ...

Embodiment 3

[0048] (1) Synthesis of ω-bromooctyltriphenylphosphonium bromide salt

[0049] Put 27.0g (100mmol) of 1,8-dibromooctane and 28.8g (110mmol) of triphenylphosphine into 300ml of benzene, heat and reflux for 24h, after the reaction is over, pour out the benzene layer, remove the remaining benzene, and obtain ω- Bromooctyltriphenylphosphonium bromide salt 48.10g, yield 90.50%.

[0050] (2) Synthesis of ω-bromododecene

[0051] Under the protection of nitrogen, add 31.92g (60mmol) ω-bromoquaternary phosphonium salt into the mixture of 30ml tetrahydrofuran and 6ml diethylene glycol dimethyl ether, stir to dissolve and maintain the temperature at 20°C-30°C, slowly add 30ml3 .0mol / L tetrahydrofuran solution of dimethyl sulfoxide sodium salt, stirred and reacted for 1.5h, then cooled to -5°C, added dropwise a mixture of 4.32g (60mmol) n-butyraldehyde and 8ml tetrahydrofuran, kept for 10h, followed by TLC detection After the reaction of the raw materials, add ice water, adjust the pH ...

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Abstract

The invention relates to a synthetic method for a (Z / E)-8-dodecylene-1-ol acetate compound. The method comprises the followings steps: enabling 1, 8-dibromooctane to react with triphenyl phosphine to produce Omega-bromo-octyl triphenylphosphonium bromide salt, then enabling the Omega-bromo-octyl triphenylphosphonium bromide salt to react with aldehyde under the action of dimethylsulfoxide sodium salt as organic base to produce Omega-brominated dodecylene, enabling the Omega-brominated dodecylene to be subjected to sodium hydroxide hydrolysis to obtain (Z / E)-8-dodecylene-1-ol, and enabling the (Z / E)-8-dodecylene-1-ol and acetic anhydride to be subjected to acetylation reaction, so as to obtain the (Z / E)-8-dodecylene-1-ol acetate compound. According to the invention, the 1, 8-dibromooctane as a raw material is easy to obtain, is stable compared with 8-bromine octanol, and cannot cause condensation reaction during the salifying process, a mixed solvent is adopted in the Wittig reaction, the dimethylsulfoxide sodium salt is adopted as organic base, so that t the Wittig reaction under low temperature and homogeneous phase is facilitated, and the fact that the ratio of cis-trans structures of the product is within an appropriate range is facilitated.

Description

technical field [0001] The invention relates to a method for synthesizing a sex pheromone of the pear borer moth, in particular a (Z / E)-8-dodecen-1-ol acetate compound, and belongs to the technical field of pesticides. Background technique [0002] Small borer moth, referred to as pear small, also known as oriental borer moth, belongs to Lepidoptera Lepidopteridae. It is distributed in the north and south fruit areas of our country, mainly harming pears and peaches, but also harming apples, hawthorns, apricots, jujubes and other fruit trees. The sex attractant trapping method has no pollution, no pollution, no harm to natural enemies and beneficial insects, and has been paid more and more attention by people. In 1969, Roelfs and others identified that the main component of the small pear borer was (Z)-8-dodecen-1-ol acetate, and later found that (E)-8-dodecen-1-ol acetate was also its One of the active ingredients, when the cis-trans molar ratio reaches 95:5, its activity ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/145C07C67/08
CPCC07C17/2635C07C29/124C07C67/08C07C69/145C07C33/025C07C21/14
Inventor 李德军张作山李旭坤陈强左伯军江忠萍韩济峰
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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