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

Method for synthesizing gamma-alkyl butyrolactone from L-glutamic acid

A technology of alkyl butyrolactone and glutamic acid, applied in the field of perfume industry, can solve the problems of triphenylphosphorus being difficult to handle, unsuitable for industrial production, dangerous in operation, etc., and achieves low price, low equipment requirements, and reduced production cost. Effect

Inactive Publication Date: 2012-10-03
龙海市贝特利生物科技有限公司
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The shortcoming of this method is, 1. adopt oxalyl chloride to prepare acyl chloride, industrial operation is more dangerous; 2. adopt silica gel column to obtain aldehyde; ; 4. The product needs to be purified by silica gel column, which is not suitable for industrial production
5. L-glutamic acid can only get γ-alkyl butyrolactone in R configuration

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
  • Method for synthesizing gamma-alkyl butyrolactone from L-glutamic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Preparation of epoxy compounds

[0038] 1. Add 400g of glutamic acid, 600mL of water and 600mL of concentrated hydrochloric acid into the reaction flask, then dropwise add 600mL of sodium nitrite solution (containing 280g of sodium nitrite), keep the reaction temperature at 0-5°C, and finish dropping in 6-8 hours , after the dropwise addition was completed, it was raised to room temperature and stirred overnight, and the water was evaporated under reduced pressure below 50°C to obtain a white salt-like viscous solid, which was extracted with 400 mL of ethyl acetate three times, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Obtain (S)-5-oxotetrahydrofuran-2-carboxylic acid; add 1L absolute ethanol and 50-80mL concentrated sulfuric acid to the crude (S)-5-oxotetrahydrofuran-2-carboxylic acid obtained above, and stir for 8~14 hours After the reaction was completed, anhydrous sodium carbonate was added to neutralize to pH = 7...

Embodiment 2

[0050] 1. Preparation of epoxy compounds

[0051] 1. Add 400g of glutamic acid, 600mL of water and 600mL of concentrated hydrochloric acid into the reaction flask, then dropwise add 600mL of sodium nitrite solution (containing 280g of sodium nitrite), keep the reaction temperature at 0-5°C, and finish dropping in 6-8 hours , after the dropwise addition was completed, it was raised to room temperature and stirred overnight, and the water was evaporated under reduced pressure below 50°C to obtain a white salt-like viscous solid, which was extracted with 400 mL of ethyl acetate three times, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Obtain (S)-5-oxotetrahydrofuran-2-carboxylic acid; add 1L absolute ethanol and 50-80mL concentrated sulfuric acid to the crude (S)-5-oxotetrahydrofuran-2-carboxylic acid obtained above, and stir for 8~14 hours After the reaction was completed, anhydrous sodium carbonate was added to neutralize to pH = 7...

Embodiment 3

[0063] 1. Preparation of epoxy compounds

[0064] 1. Add 400g of glutamic acid, 600mL of water and 600mL of concentrated hydrochloric acid into the reaction flask, then dropwise add 600mL of sodium nitrite solution (containing 280g of sodium nitrite), keep the reaction temperature at 0-5°C, and finish dropping in 6-8 hours , after the dropwise addition was completed, it was raised to room temperature and stirred overnight, and the water was evaporated under reduced pressure below 50°C to obtain a white salt-like viscous solid, which was extracted with 400 mL of ethyl acetate three times, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Obtain (S)-5-oxotetrahydrofuran-2-carboxylic acid; add 1L absolute ethanol and 50-80mL concentrated sulfuric acid to the crude (S)-5-oxotetrahydrofuran-2-carboxylic acid obtained above, and stir for 8~14 hours After the reaction was completed, anhydrous sodium carbonate was added to neutralize to pH = 7...

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 method for synthesizing gamma-alkyl butyrolactone from L-glutamic acid. The method disclosed by the invention comprises the following steps: (1) the L-glutamic acid is hydroxylated to obtain (S)-5-oxo tetrahydrofuran-2-formic acid, and the (S)-5-oxo tetrahydrofuran-2-formic acid is esterified to obtain (R)-2-hydroxy-1, 6-diethyl adipate; (2) the (R)-2-hydroxy-1, 6-diethyl adipate is reduced to obtain (S)-5-hydroxymethyl dihydrofuran-2 (3H)-ketone; (3) the (S)-5-hydroxymethyl dihydrofuran-2 (3H)-ketone is sulfonated to obtain (S)-(5-oxo tetrahydrofuran group)-4-methyl p-methyl toluenesulfonate, and the (S)-(5-oxo tetrahydrofuran group)-4-methyl p-methyl toluenesulfonate is epoxidized to obtain (S)-4, 5-epoxy-methyl pentanoate; and (4) the (S)-4, 5-epoxy-methyl pentanoate is used as a raw material for synthesizing the gamma-alkyl butyrolactone. The method disclosed by the invention has the characteristics that the production cost is low, production can be carried out according to the needs of customers, the flexibility is very high, the safety is good, the requirement on equipment is low, and the method is very suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of perfume industry, in particular to a method for synthesizing gamma-alkyl butyrolactone with L-glutamic acid. Background technique [0002] γ--Alkyl lactone series compounds are widely used as spices, and are widely used in food flavors and fragrances. In recent years, due to the requirement of returning to nature and pursuing health, natural chiral γ-alkyl butyrolactone fragrances have attracted more attention, mainly because of natural chiral γ-alkyl butyrolactone, no matter in aroma or They are far superior to synthetic fragrances in terms of safety in use. [0003] In the prior art, the methods for synthesizing chiral γ-alkyl butyrolactone mainly contain the following: [0004] 1. Split method [0005] Japan Soda Fragrance Co., Ltd. reported in the form of a patent that the carboxyl group in the racemic hydroxy acid produced after hydrolysis is resolved with an optically active base to obtain optically active...

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): C07D307/33
Inventor 王少培杨景祥黄志强
Owner 龙海市贝特利生物科技有限公司
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