Preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate

A technology of dimethyl cyclopentyl malonate and dimethyl malonate, which is applied in the field of catalysis, can solve the problems of large amount of catalyst, corrosive equipment, and unfriendly environment, so as to reduce equipment investment and waste water , post-processing simple effects

Active Publication Date: 2020-09-11
SHANDONG NHU PHARMA
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses a large amount of catalyst, is corrosive to the equipment, and cannot be recycled. The post-treatment process produces a large amount of salty wastewater, which is not friendly to the environment.

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
  • Preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate
  • Preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate
  • Preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] (1) Preparation of intermediate 3-(3-oxo-2-pentyl) dimethyl cyclopentylmalonate

[0065] Take by weighing 100g methyl alcohol, 2.63g rhodium chloride hydrate (0.01mol), 11.52g bis-diphenylphosphine methane (the mol ratio of rhodium chloride and bis-diphenylphosphine methane is 1:3) in there-necked flask, under nitrogen Under the atmosphere, the temperature was raised to 30°C and stirred for 60min to prepare a transition metal complex catalyst; the temperature of the transition metal complex catalyst solution was lowered to 0°C, and 152g (1mol) of 2-pentyl-2-cyclopentenone, acetone, and Dimethyl diacid 145.2g (1.1mol), L-proline 3.45g (the molar ratio of catalyst and L-proline is 1:3), keep warm for 3 hours, GC detects the content of reaction solution, 2-pentyl - If the total residual amount of 2-cyclopentenone is less than or equal to 0.5%, stop the reaction.

[0066] Rectification gives intermediate 3-(3-oxo-2-pentyl) dimethyl cyclopentylmalonate 268.68g, GC content 9...

Embodiment 2

[0070] (1) Preparation of intermediate 3-(3-oxo-2-pentyl) dimethyl cyclopentylmalonate

[0071] Take by weighing 100g dichloromethane, 2.07g ruthenium trichloride (0.01mol), 19.92g1,2-bisdiphenylphosphine ethane (the molar ratio of ruthenium trichloride and 1,2-bisdiphenylphosphine ethane 1:5) in a three-necked flask, heated to 20°C under nitrogen atmosphere and stirred for 80 minutes to prepare a transition metal complex catalyst; cool the transition metal complex catalyst solution to -2°C, and add 2-pentyl -2-cyclopentenone 152g (1mol), dimethyl malonate 198g (1.5mol), L-phenylalanine 8.26g (the molar ratio of catalyst and L-phenylalanine is 1:5), Incubate for 4 hours, detect the content of the reaction solution by GC, if the total residual amount of 2-pentyl-2-cyclopentenone is ≤0.5%, stop the reaction.

[0072] Rectification obtains intermediate 3-(3-oxo-2-pentyl) dimethyl cyclopentylmalonate 272.16g, GC content 98.69%, reaction process yield is 94.46% (according to 2-pen...

Embodiment 3

[0076] (1) Preparation of intermediate 3-(3-oxo-2-pentyl) dimethyl cyclopentyl malonate

[0077] Take by weighing 100g toluene, 7.85g copper acetylacetonate (0.03mol), 83.66g1,2-bisdiphenylphosphine ethane (the molar ratio of acetylacetonate copper and 1,2-bisdiphenylphosphine ethane is 1:7 ) in a three-necked flask, heated to 40°C and stirred for 80 minutes under nitrogen atmosphere to prepare a transition metal complex catalyst; cool the transition metal complex catalyst solution to -5°C, and add 2-pentyl-2-cyclo Pentenone 152g (1mol), dimethyl malonate 396g (3.0mol), L-4-hydroxyproline 31.47g (the molar ratio of catalyst and L-4-hydroxyproline is 1:8), Incubate for 5 hours, detect the content of the reaction solution by GC, if the total residual amount of 2-pentyl-2-cyclopentenone is ≤0.5%, stop the reaction.

[0078] The rectification obtained 266.42 g of the addition reaction intermediate, the GC content was 98.14%, and the reaction process yield was 91.95% (based on 2-p...

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 relates to a preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. The preparation method of the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate comprises the following step: in the presence of a transition metal complex and a catalytic additive, reacting 2-pentyl-2-cyclopentenone with dimethyl malonate in a reaction solvent to obtain the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. According to the preparation method provided by the invention, a sodium methoxide strong base catalyst is not needed, the generation of salt-containing wastewater is avoided, the method is environment-friendly and high in yield, and meanwhile, the recycling of the catalyst is realized.

Description

technical field [0001] The invention relates to the technical field of catalysis, in particular to a preparation method of dimethyl 3-(3-oxo-2-pentyl)cyclopentylmalonate. Background technique [0002] Methyl dihydrojasmonate is a colorless to light yellow liquid with elegant and soft jasmine fragrance and long-lasting fragrance, as well as fresh orchid fragrance and comfortable lemon-like fruity fragrance. The whole fragrance is light and elegant, volatile It is slow and gentle, with long-lasting fragrance and good fragrance adjustment effect. It is widely used in the formulation of cosmetic essence and soap essence, and is an important synthetic fragrance. [0003] The demand for methyl dihydrojasmonate is increasing day by day, prompting people to constantly search for more economical methods, optimize the process route and reduce costs. Dimethyl (3-oxo-2-pentyl)cyclopentylmalonate is an important intermediate of methyl dihydrojasmonate, 3-(3-oxo-2-pentyl)cyclopentylmalon...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/347C07C67/32C07C69/716B01J31/24
CPCC07C67/347C07C67/54C07C67/32B01J31/24C07C2601/08B01J2231/32B01J2531/822B01J2531/821B01J2531/16B01J2531/847B01J2531/845B01J2531/26B01J2531/72B01J2531/64B01J2531/827B01J2531/824C07C69/716Y02P20/584
Inventor 马慧娟马啸宦关生李孟杰李庆辉于明姜晓阳黄珊珊
Owner SHANDONG NHU PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap