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

Resolution method of 3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid

A technology of dimethylcyclopropane carboxylic acid and acetyl group, which is applied in the field of resolution of 3-acetyl-2,2-dimethylcyclopropane carboxylic acid, can solve the problem of light instability, light stability, Problems such as complex production routes and poor safety, etc., achieve the effects of easy operation, high optical purity, and mild reaction conditions

Pending Publication Date: 2022-05-13
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Extracting pyrethrins from pyrethrum flowers is not only costly, but also cannot meet the needs of various parties. Therefore, when the structure of pyrethrins was determined, scholars from various countries began to screen and synthesize pyrethrins by changing the structures of the acid part and the alcohol part respectively. Finding New Pesticides
[0003] Pyrethroids have been developed to this day, and have experienced successively from light instability to light stability (Ding Zhizhi, Liu Jikai, Ding Jingao, Gu Kun. Research progress of pyrethroids, Yunnan Chemical Industry, 2001, 28 (2): 22 -24.), from cyclopropane structure to acyclic structure (Chen Wanyi, Xue Zhenxiang, Wang Nengwu. Research and Development of New Pesticides Beijing Chemical Industry Press, 1995, 178-209.), from carboxylate to non-carboxylate (Liu Aiping. Progress in research on non-carboxylate pyrethroids, Hunan Chemical Industry, 2000, 30(5):4-7.), and a series of processes such as the introduction of fluorine-containing groups and heterocyclic structures (Yang Guichun, Cheng Shiyuan, Chen Zuxing, etc. .Synthetic Applied Chemistry of New Non-ester Pyrethroids, 2001, 8:678-680.), although there are some pyrethroid compounds to choose from at present, but the production route is complicated, the cost is high, and the safety is poor. Some old products Drug resistance has emerged

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
  • Resolution method of 3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid
  • Resolution method of 3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid
  • Resolution method of 3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] (1) Add 31.2 g of water to the reactor, and then add 15.6 g of 3-acetyl-2,2-dimethylcyclopropanecarboxylic acid.

[0033] (2) In the stirring state, add 25% ammonia water to the reaction kettle, the pH value of the condition system is 7, then start to lower the temperature, and the temperature drops to 10°C.

[0034] (3) When the temperature drops to 10°C, keep warm for the reaction.

[0035] (4) Add 8.58 g of chiral resolving agent (S)-(-)-1-(p-toluene)ethylamine hydrochloride (2a) into the reaction kettle, then add 8.58 g of water, and dissolve under stirring.

[0036] (5) Slowly add the aqueous solution of the resolving agent in (4) to (3) dropwise, and continue to keep stirring at 10°C for 2 hours after the dropwise addition, there will be Methyl cyclopropane carboxylic acid double salt generation.

[0037] (6) Filter, add dilute acid to the mother liquor to adjust the pH to 3, stir at 10°C for 1 hour, filter, the solid is racemic 3-acetyl-2,2-dimethyl...

Embodiment 2

[0041]

[0042] (1) Add 31.2 g of water to the reactor, and then add 15.6 g of 3-acetyl-2,2-dimethylcyclopropanecarboxylic acid.

[0043] (2) In the stirring state, add 25% ammonia water to the reaction kettle, the pH value of the condition system is 7, then start to lower the temperature, and the temperature drops to 10°C.

[0044] (3) When the temperature drops to 10°C, keep warm for the reaction.

[0045] (4) Add 10.13 g of chiral resolving agent (S)-(+)-Alpha-methyl-4-nitrobenzylamine hydrochloride (2b) into the reaction kettle, then add 10.13 g of water, and dissolve under stirring clear.

[0046] (5) Slowly add the aqueous solution of the resolving agent in (4) to (3) dropwise, and continue to keep stirring at 10°C for 2 hours after the dropwise addition, there will be Methyl cyclopropane carboxylic acid double salt generation.

[0047](6) Filter, add dilute acid to the mother liquor to adjust the pH to 3, stir at 10°C for 1 hour, filter, the solid is racemic 3-ace...

Embodiment 3

[0050]

[0051] (1) Add 31.2 g of water to the reactor, and then add 15.6 g of 3-acetyl-2,2-dimethylcyclopropanecarboxylic acid.

[0052] (2) In the stirring state, add 25% ammonia water to the reaction kettle, the pH value of the condition system is 7, then start to lower the temperature, and the temperature drops to 10°C.

[0053] (3) When the temperature drops to 10°C, keep warm for the reaction.

[0054] (4) Add 8.68 g of chiral resolving agent (S)-4-(1-aminoethyl)phenol hydrochloride (2c) into the reaction kettle, then add 8.68 g of water, and dissolve under stirring.

[0055] (5) Slowly add the aqueous solution of the resolving agent in (4) to (3) dropwise, and continue to keep stirring at 10°C for 2 hours after the dropwise addition, there will be Methyl cyclopropane carboxylic acid double salt generation.

[0056] (6) Filter, add dilute acid to the mother liquor to adjust the pH to 3, stir at 10°C for 1 hour, filter, the solid is racemic 3-acetyl-2,2-dimethylcyclo...

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 resolution method of 3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid, and belongs to the field of organic synthesis. The invention discloses a method for preparing trans-dextro 3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid through resolution and a preparation method of the trans-dextro 3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid. According to the invention, a chiral phenylethylamine derivative resolving agent is used for resolving the compound 1, so that the compound 1 with high optical purity is obtained at high yield. The reaction conditions in the resolution process are mild, the resolution efficiency is high, the recovery rate of the resolving agent is high, and the obtained trans-dextro-3-acetyl-2, 2-dimethyl cyclopropane carboxylic acid is high in optical purity.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a resolution method for 3-acetyl-2,2-dimethylcyclopropanecarboxylic acid. Background technique [0002] Pyrethroids are synthetic insecticides that imitate the structure of natural pyrethrum flowers. They have the characteristics of high efficiency, low toxicity, low residue, and good environmental compatibility. They are currently a class of compounds advocated by the international pesticide industry. Extracting pyrethrins from pyrethrum flowers is not only costly, but also cannot meet the needs of various parties. Therefore, when the structure of pyrethrins was determined, scholars from various countries began to screen and synthesize pyrethrins by changing the structures of the acid part and the alcohol part respectively. Find new insecticides. [0003] Pyrethroids have been developed to this day, and have experienced successively from light instability to light st...

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): C07C51/41C07C51/02C07C51/48C07C62/18
CPCC07C51/412C07C51/02C07C51/48C07B2200/07C07C2601/02C07C62/18
Inventor 胡向平陈松
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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