Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

The synthetic method of z7,9-decadiene-1-alcohol

A synthesis method and decadiene technology are applied in the field of chemical synthesis of insect sex pheromones, can solve the problems of difficult products in the synthesis method, separation of intermediate products, long synthesis routes, etc., and achieve low cost, short reaction time, and less three wastes. Effect

Inactive Publication Date: 2017-04-12
SHANXI AGRI UNIV
View PDF1 Cites 0 Cited by
  • 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. However, it is difficult to obtain products by the synthesis method of terminally conjugated diene sex semiochemicals. At the same time, there are too long synthetic routes, low yields, and toxic solvents. , cumbersome operation and the need to separate intermediate products, etc.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • The synthetic method of z7,9-decadiene-1-alcohol
  • The synthetic method of z7,9-decadiene-1-alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] (1) Synthesis of 7-hydroxyl-1-heptanal

[0015] Add ground PCC (9.5g, 44.2mmol),

[0016] Silica gel 9.5 g in 95 mL of anhydrous carbon dichloride. Under nitrogen protection, 1,7-heptanediol (5.80g, 43.9mmol) was quickly

[0017] Add quickly and keep stirring, react at room temperature for 3h, then add 19mL of distilled water and then add 95mL of diethyl ether for extraction, and then stir

[0018] 30min, then use silica gel suction filtration, transfer the filtrate to a separatory funnel, add dropwise 20% sodium hydroxide to make the filtrate neutral, extract with ether

[0019] Take three times and combine the organic phases, wash three times with saturated sodium chloride, dry over anhydrous sodium sulfate for 12 hours, evaporate the solvent, and separate the residue with silica gel column to obtain 4.25 g of 7-hydroxy-1-heptanal, with a yield of 73.3%.

[0020] (2) Synthesis of Z7,9-decadien-1-ol

[0021] Add allyl triphenyl

[0022] Phosphine bromide (2.9 g, 8...

Embodiment 2

[0024] (1) Synthesis of 7-hydroxyl-1-heptanal

[0025] Add ground PCC (12.9 g, 60.0 mmol), 12.9 g of silica gel and 90.3 mL of anhydrous carbon dichloride into a 500 mL standard ground three-neck flask equipped with a reflux condenser. Under the protection of nitrogen, 1,7-heptanediol (6.58g, 49.85mmol) was added quickly and kept stirring, reacted at room temperature for 1h, then added 27.1mL of distilled water and 90.3mL of diethyl ether for extraction, stirred for 50min, and then used Silica gel suction filtration, transfer the filtrate to a separatory funnel, add 20% sodium hydroxide dropwise to make the filtrate neutral, extract three times with ether and combine the organic phases, wash three times with saturated sodium chloride, dry over anhydrous sodium sulfate for 12 hours, evaporate The solvent was removed, and the residue was separated with a silica gel column to obtain 4.53 g of 7-hydroxy-1-heptanal, with a yield of 68.6%.

[0026] (2) Synthesis of Z7,9-decadien-1-...

Embodiment 3

[0029] (1) Synthesis of 7-hydroxyl-1-heptanal

[0030] Add ground PCC (16.0g, 77.4mmol), 16.0g of silica gel and 136mL of anhydrous carbon dichloride into a 500mL standard ground three-neck flask equipped with a reflux condenser, and stir thoroughly for 30 min. , add 1,7-heptanediol (9.0g, 68.18mmol) quickly, and keep stirring, react at room temperature for 2h, then add 34mL of distilled water and then add 130mL of diethyl ether for extraction, and then stir for 40min, and then use silica gel to filter the filtrate Transfer to a separatory funnel, add 20% sodium hydroxide dropwise to make the filtrate neutral, extract three times with ether and combine the organic phases, wash three times with saturated sodium chloride, dry over anhydrous sodium sulfate for 12 hours, evaporate the solvent, and the residue is washed with silica gel Column separation yielded 6.45 g of 7-hydroxyl-1-heptanal, with a yield of 71.7%.

[0031] (2) Synthesis of Z7,9-decadien-1-ol

[0032] In a 250mL...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesizing method of Z7,9-decadiene-1-ol. The method comprises the following two steps: (1) 7-hydroxy-1-heptanal is synthesized with 1,7-heptanediol as a raw material; and (2) Z7,9-decadiene-1-ol is synthesized. The method has the advantages of mild synthesis conditions, short reaction time, simple operation, wide application range, shortened process flow, high yield, low cost, less three-waste generation, and easy industrialization. During the 7-hydroxy-1-heptanal synthesis reaction, silica gel is added, such that PCC dispersion is facilitated, and PCC dissolution in dichloromethane is promoted. The reaction is carried out under room temperature, such that energy is saved. When the reaction is finished, diethyl ether and water are added for extraction, such that reaction product yield is improved. During the Z7,9-decadiene-1-ol synthesis process, a phase transfer catalyst 18-crown ether-6 and a nonpolar solvent benzene are adopted, and a cis product is obtained through the reaction. A weak base potassium carbonate is adopted, such that hydroxyl group protection of 7-hydroxy-1-heptanal is avoided. The method provided by the invention has one step less than existing methods of using strong bases such as phenyl lithium.

Description

technical field [0001] The present invention relates to a chemical synthesis method of insect sex pheromone, in particular to a chemical synthesis method of Z7,9-decadien-1-ol, an important component of the sex pheromone of the green moth. Background technique [0002] Latoia lepida (Cramer) belongs to Lepidoptera (Lepidoptera), Limacodidae (Limacodidae), distributed in China from Heilongjiang in the north, to Taiwan, Hainan, Guangdong, Guangxi, and Yunnan in the south, and from the national border in the east. West from Shaanxi, Gansu into Sichuan. Harm forest belts, street trees, garden trees and economic forest fruit trees and other trees. The damage is mainly caused by larvae biting leaves. Young larvae eat mesophyll, resulting in translucent withered yellow spots on leaves; Branches or even whole tree leaves are eaten up and only veins are left or polished rods, which affect tree growth, yield and viewing. At the same time, the venomous stingers on the larvae of the ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C33/02C07C29/34C07C47/19C07C45/30
CPCC07C29/34C07C45/305C07C33/02C07C47/19
Inventor 杨淑珍张金桐靳泽荣刘红霞刘志雄
Owner SHANXI AGRI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com