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Synthesis method of Z9,11-dodecadienol acetate

A technology of carbadienol acetate and dodecadienol, which is applied in the preparation of carboxylate, the preparation of carbon-based compounds, chemical instruments and methods, etc. Long and other problems, to achieve the effects of mild synthesis conditions, low cost and short reaction time

Inactive Publication Date: 2015-11-18
SHANXI AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a variety of sex attractants have been synthesized by artificial synthesis and have been commercialized, but the synthesis method of terminal conjugated diene sex semiochemicals is too long, the yield is not high, the reaction conditions are harsh, the operation is cumbersome, and it is easy to cause accidents , higher energy consumption and other disadvantages

Method used

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  • Synthesis method of Z9,11-dodecadienol acetate
  • Synthesis method of Z9,11-dodecadienol acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] (1) Synthesis of 9-hydroxyl-1-nonanal

[0016] Add 5.4g of 1,9-nonanediol and 81mL of anhydrous dichloromethane to a 500mL standard ground three-neck flask equipped with a reflux condenser, stir electrically, and add 7.02g of PCC in three equal batches under nitrogen protection. and 7.02g of silica gel, after adding all the reactants, continue to react at room temperature for 1h, then add 16.2mL of distilled water and then add 81mL of ether, stir and extract for 40min, then use silica gel for suction filtration, transfer the filtrate to a separatory funnel, add 20% Sodium hydroxide made the filtrate neutral, extracted three times with ether and combined the organic phases, washed three times with saturated sodium chloride, dried over anhydrous sodium sulfate for 12 hours, evaporated the solvent, and separated the residue with a silica gel column to obtain 9-hydroxy-1-nonane Aldehyde 4.0g, the yield is 74.1%.

[0017] (2) Synthesis of Z9,11-dodecadienol

[0018] In a 2...

Embodiment 2

[0022] (1) Synthesis of 9-hydroxyl-1-nonanal

[0023] Add 8.0g of 1,9-nonanediol and 96mL of anhydrous dichloromethane to a 500mL standard ground three-neck flask equipped with a reflux condenser, stir electrically, and add 12.8g of PCC in three batches of equal mass under nitrogen protection. and 12.8g of silica gel, after all the addition, the reactant continued to react at room temperature for 3h, then added 28.8mL of distilled water and then 96mL of ether, stirred and extracted for 60min, then filtered with silica gel, transferred the filtrate to a separatory funnel, and added 20% Sodium hydroxide made the filtrate neutral, extracted three times with ether and combined the organic phases, washed three times with saturated sodium chloride, dried over anhydrous sodium sulfate for 12 hours, evaporated the solvent, and separated the residue with a silica gel column to obtain 9-hydroxy-1-nonane Aldehyde 5.51g, the yield is 68.9%.

[0024] (2) Synthesis of Z9,11-dodecadienol

...

Embodiment 3

[0029] (1) Synthesis of 9-hydroxyl-1-nonanal

[0030] Add 7.5g of 1,9-nonanediol and 105mL of anhydrous dichloromethane into a 500mL standard three-neck flask with a reflux condenser, add 10.5g of PCC in three batches under the protection of nitrogen and 10.5g of silica gel, after adding all the reactants, continue to react at room temperature for 2h, then add 25mL of distilled water and then add 105mL of diethyl ether, stir and extract for 50min, then use silica gel for suction filtration, transfer the filtrate to a separatory funnel, add 20% hydrogen dropwise Sodium oxide made the filtrate neutral, extracted three times with ether and combined the organic phases, washed three times with saturated sodium chloride, dried over anhydrous sodium sulfate for 12 hours, evaporated the solvent, evaporated the solvent, and separated the residue with a silica gel column to obtain 9-hydroxy- 1-Nonanal 5.44g, the yield is 72.6%.

[0031] (2) Synthesis of Z9,11-dodecadienol

[0032] In a ...

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Abstract

The invention discloses a synthesis method of Z9,11-dodecadienol acetate. The synthesis method comprises the following steps: (1) by taking 1,9-nonanediol as a raw material, performing unilateral oxidation to synthesize 9-hydroxyl-1-nonanal; (2) synthesizing an intermediate Z9,11-dodecadienol; (3) synthesizing the Z9,11-dodecadienol acetate. The synthesis method has the advantages of mild synthesis conditions, short reaction time, easy operation, wide application range, high yield, low cost and easy industrialization, the process flow is shortened, and three wastes are few. In a synthesis reaction of the 9-hydroxyl-1-nonanal, silica gel is added, the dispersion of PCC (Pyridinium Chlorochromate) is facilitated, the opportunity of oxidation of two hydroxyls is reduced by adding the PCC in batches, the reaction is performed at room temperature, and energy is saved; after the reaction is completed, ethyl ether and water are added for extraction, and the yield of reactants is improved. In the synthesis process of the Z9,11-dodecadienol, a phase transfer catalyst 18-crown ether-6 and non-polar solvent benzene are adopted to react so as to obtain a cis-product; meanwhile, weak alkali potassium carbonate is adopted, so that the protection of the hydroxyls of the 9-hydroxyl-1-nonanal is avoided, and a reaction synthesis route is shortened.

Description

technical field [0001] The invention relates to a method for synthesizing chemical components of insect sex pheromones, in particular to a method for synthesizing Z9,11-dodecadienol acetate, an important component of sex pheromones of tortrix moths. Background technique [0002] The crop yield reduction caused by various pests in the world is as high as more than one-third of the overall yield, causing serious economic losses. With the progress of society and the change of human concept, pest control strategies are increasingly developing in the direction of pest management (SPM), ecological management (EPM), and sustainable management (SPM). In the process of agricultural production, green biological control technology is gradually replacing traditional chemical control, and has become a research hotspot in integrated pest control. [0003] Trapping and killing insects with chemically synthesized sexual attractants is a new pest control technology with high efficiency, str...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/145
CPCC07C29/38C07C45/292C07C67/08C07C47/19C07C33/02C07C69/145
Inventor 杨淑珍张金桐靳泽荣刘红霞刘志雄
Owner SHANXI AGRI UNIV
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