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

Method used for synthesis of 6-hydroxyl-2, 3, 4-triethoxy-alpha-chloroacetophenone

A technology of chlorinated acetophenone and trimethoxyphenol, applied in the direction of condensation preparation of carbonyl compounds, organic chemistry, etc., can solve the problems of unindustrialized large-scale production, corrosive equipment, difficult to control, etc., and achieve cost saving, simple raw materials, The effect of simple post-processing methods

Inactive Publication Date: 2019-11-26
NANHUA UNIV
View PDF13 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has certain adaptability for the preparation of α-chloroacetophenones substituted by hydroxyl groups at different positions, it is only suitable for several special cases such as resorcinol, and the corresponding method cannot be obtained for p-triphenol. The finished product of chloroacetophenone; secondly, the continuous flow of hydrogen chloride is also relatively cumbersome, and it is also corrosive to the equipment. The reaction needs to be reacted in a continuous low temperature environment for 6 hours, which is not easy to control, and moreover, it needs to be continuously cooled and crystallized , itself also causes a certain energy loss, and the final total yield is also low, so it is not suitable for industrialized large-scale production

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 used for synthesis of 6-hydroxyl-2, 3, 4-triethoxy-alpha-chloroacetophenone
  • Method used for synthesis of 6-hydroxyl-2, 3, 4-triethoxy-alpha-chloroacetophenone
  • Method used for synthesis of 6-hydroxyl-2, 3, 4-triethoxy-alpha-chloroacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The influence of embodiment 1 different reaction temperature on reaction yield

[0038] Because in the prior art, when carrying out Friedel-Crafts acylation reaction, common reaction system is to use aluminum chloride as catalyst, with nitrobenzene as reaction solvent, therefore, the applicant adopts this reaction system, first investigated different temperature for influence on the yield of the reaction. The specific operation is as follows:

[0039] Weigh (10mmol, 1.84g) 3,4,5-trimethoxyphenol and dissolve it in (20ml) nitrobenzene, slowly add (10mmol, 1.13g) chloroacetyl chloride dropwise in the constant pressure dropping funnel, dropwise Finally, rinse the dropping funnel with 5ml of nitrobenzene, drop the remaining chloroacetyl chloride on the wall into the reaction flask, then add (10mmol, 1.33g) aluminum chloride anhydrous, install a condensation reflux and drying device, Stir and heat the reaction in oil baths at different temperatures, and detect the reaction...

Embodiment 2

[0042] The influence of embodiment 2 different solvents on reaction

[0043] Weigh (10mmol, 1.84g) 3,4,5-trimethoxyphenol and dissolve it in (20ml) different reaction solvents, slowly add (10mmol, 1.13g) chloroacetyl chloride dropwise in the constant pressure dropping funnel, dropwise Finally, rinse the dropping funnel with 5ml of different reaction solvents, drop the remaining chloroacetyl chloride on the wall into the reaction flask, then add (10mmol, 1.33g) anhydrous aluminum chloride, install a condensing reflux and drying device, and adjust the oil bath The pot controls the temperature of the reaction solution at 40° C. and heats the reaction with airtight stirring. The reaction is detected by TLC. After the reaction is completed, 6-hydroxy-2,3,4-trimethoxy-α-chloroacetophenone is obtained after post-processing and purification. Yield (based on 3,4,5-trimethoxyphenol) is as follows:

[0044] solvent Nitrobenzene Dichloromethane acetone Yield / % 62.1 ...

Embodiment 3

[0047] The influence of embodiment 3 different acylating reagents on reaction

[0048] Weigh (10mmol, 1.84g) 3,4,5-trimethoxyphenol and dissolve it in (20ml) dichloromethane, slowly add (10mmol) different acylating reagents dropwise in the constant pressure dropping funnel, and use Rinse the dropping funnel with 5ml of dichloromethane, drop the residual acylating reagent on the wall into the reaction flask, then add (10mmol, 1.33g) aluminum chloride anhydrous, install a condensation reflux and drying device, adjust the oil bath to The temperature of the reaction solution was controlled at 40°C and the reaction was heated with airtight stirring, and the reaction was detected by TLC. After the reaction was completed, the reaction solution was poured into concentrated hydrochloric acid: ice water (1:1), vigorously stirred, acidolysis and cooling, and the solid was precipitated after standing still. Filter, wash with saturated sodium chloride solution until neutral, and vacuum-dry...

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 used for synthesis of 6-hydroxyl-2, 3, 4-triethoxy-alpha-chloroacetophenone. According to the method, 3, 4, 5-trimethoxyphenol is taken as a raw material, a Lewis acidis taken as a catalyst, dichloromethane is taken as a reaction solvent, chloroacetyl chloride is taken as an acylation agent, stirring reaction is carried out, after reaction, post-treatment purification is carried out so as to obtain a target product. The method is capable of producing single acetoxylation products at a relatively high yield, product purity is high, and generation of di-substituted side products is avoided; post-treatment method is simple; precipitation of products in solid state can be realized; operation such as column chromatography is not needed; operation steps are reduced; and production cost is reduced.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 6-hydroxy-2,3,4-trimethoxy-α-chloroacetophenone. Background technique [0002] As a fine chemical product, α-chloroacetophenone is mainly used as a pharmaceutical intermediate. It can be used for the synthesis of various structurally modified flavonoids. The development of this functional product has broad application prospects. Research The synthetic route of this compound is extremely important. [0003] The synthetic route of the α-chloroacetophenone reported in the prior art mainly contains following several kinds: [0004] [0005] This method is to add acetophenone into the reaction pot, feed chlorine gas, react at 60-70°C, heat up to 80°C after feeding chlorine gas, evaporate low boiling substances under reduced pressure, cool to below 5°C, and stand for 48 hours. Crystals were precipitated and filtered to obtain α-chloroacetophenone. This m...

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): C07C45/46C07C49/84C07D311/32C07D405/04
CPCC07C45/46C07D311/32C07D405/04C07C49/84
Inventor 唐国涛刘仁波邓湘萍赵婧铎彭怡娇邹阳陈妙佳
Owner NANHUA 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