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

Method for synthesizing 3,4-bis(3,4,5-trimethoxyphenyl)-2,5-diphenylcyclopentadienone

A technology of diphenylcyclopentadienone and trimethoxyphenyl, which is applied in the field of organic compound synthesis, can solve the problems of high price of reaction raw materials, cumbersome and time-consuming steps, and limited application, so as to achieve safe and reliable reaction process and comprehensive synthesis. Simple process and good reproducibility

Inactive Publication Date: 2016-05-25
SHANDONG UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is not only cumbersome and time-consuming, but also the relatively high price of the reaction raw materials and the harm to the human body and the environment also limit its industrial application.

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 3,4-bis(3,4,5-trimethoxyphenyl)-2,5-diphenylcyclopentadienone
  • Method for synthesizing 3,4-bis(3,4,5-trimethoxyphenyl)-2,5-diphenylcyclopentadienone
  • Method for synthesizing 3,4-bis(3,4,5-trimethoxyphenyl)-2,5-diphenylcyclopentadienone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Preparation of 4,4'-bis(3,4,5-trimethoxy)benzoin

[0035] Add vitamin B to the three-neck round bottom flask equipped with reflux condensation, stirring device and thermometer in sequence 1 2g, 5mL of distilled water, 16mL of ethanol, and 15.3g of 3,4,5-trimethoxybenzaldehyde, and slowly stirred in an ice-water bath for 15min. Then add 3.0 mol / L sodium hydroxide ethanol solution dropwise through the condenser to adjust the pH value of the solution to 8, and continuously add 3.0 mol / L sodium hydroxide ethanol solution to keep the pH value of the solution for 45 minutes. After heating to 55°C for 3h, cool to room temperature. After standing for 24 hours, suction filtration, the filter cake was washed 3 times with distilled water, and the filtrate was neutral to obtain a yellow solid. After recrystallization with ethanol, 9.2g of 4,4'-bis(3,4,5-trimethoxy)benzoin was obtained, the yield was 60.2%, m.p: 165.2-165.6°C (literature value (WO2010050720A2): 165-166 ℃).

...

Embodiment 2

[0045] (1) Preparation of 4,4'-bis(3,4,5-trimethoxy)benzoin

[0046] Add vitamin B to the three-neck round bottom flask equipped with reflux condensation, stirring device and thermometer in sequence 1 4g, 10mL of distilled water, 32mL of ethanol, 30.6g of 3,4,5-trimethoxybenzaldehyde, and slowly stir in an ice-water bath for 15min. Then add 3.0 mol / L sodium hydroxide ethanol solution dropwise through the condenser to adjust the pH value of the solution to 8, and continuously add 3.0 mol / L sodium hydroxide ethanol solution to keep the pH value of the solution for 45 minutes. After heating to 65°C for 3h, cool to room temperature. After standing for 24 hours, suction filtration, the filter cake was washed 3 times with distilled water, and the filtrate was neutral to obtain a yellow solid. After recrystallization from ethanol, 19.2g of 4,4'-bis(3,4,5-trimethoxy)benzoin was obtained, with a yield of 62.8%, m.p: 165.2-165.6°C.

[0047] (2) Preparation of 4,4'-bis(3,4,5-trimethox...

Embodiment 3

[0052] (1) Preparation of 4,4'-bis(3,4,5-trimethoxy)benzoin

[0053] Add vitamin B to the three-neck round bottom flask equipped with reflux condensation, stirring device and thermometer in sequence 1 2g, 5mL of distilled water, 16mL of ethanol, and 15.3g of 3,4,5-trimethoxybenzaldehyde, and slowly stirred in an ice-water bath for 15min. Then add 3.0 mol / L sodium hydroxide ethanol solution dropwise through the condenser to adjust the pH value of the solution to 8, and continuously add 3.0 mol / L sodium hydroxide ethanol solution to keep the pH value of the solution for 45 minutes. After heating to 75°C for 3h, cool to room temperature. After standing for 24 hours, suction filtration, the filter cake was washed 3 times with distilled water, and the filtrate was neutral to obtain a yellow solid. After recrystallization from ethanol, 9.0 g of 4,4'-bis(3,4,5-trimethoxy)benzoin was obtained with a yield of 58.9%, m.p: 165.2-165.6°C.

[0054] (2) Preparation of 4,4'-bis(3,4,5-trim...

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 3, 4-di(3, 4, 5-trimethoxy phenyl)-2, 5-diphenyl cyclopentadienone. The method comprises the following steps: carrying out condensation reaction on 3, 4, 5-trimethoxy benzaldehyde serving as a raw material in the presence of vitamin B1 serving as a catalyst under an alkaline condition to prepare 4, 4'-di(3, 4, 5-trimethoxy) benzoin; then, in a glacial acetic acid solution, oxidizing 4, 4'-di(3, 4, 5-trimethoxy) benzoin in the presence of copper acetate and ammonium nitrate serving as cooxidation agents to obtain 4, 4'-di(3, 4, 5-trimethoxy) benzoin; and finally, by using ethanol as a solvent and under a potassium hydroxide alkaline condition, carrying out condensation reaction on 4, 4'-di(3, 4, 5-trimethoxy) benzoin and dibenzyl ketone to prepare 3, 4-di(3, 4, 5-trimethoxy phenyl)-2, 5-diphenyl cyclopentadienone. According to the method disclosed by the invention, the reaction raw materials are cheap and easily available, the synthesis steps are simple, the reaction time is short, the reaction conditions are mild and the reaction process is easy to control; therefore, the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 3,4-bis(3,4,5-trimethoxyphenyl)-2,5-diphenylcyclopentadienone, belonging to the technical field of organic compound synthesis. Background technique [0002] Polyaryl substituted cyclopentadienones are an important class of intermediates in organic synthesis. As a raw material for organic synthesis, the two C=C conjugated double bonds on the cyclopentadienone ring can almost undergo Diels-Alder addition reaction with any unsaturated bond. One of the convenient methods. In the production of industrialized fine chemicals, polyaryl-substituted cyclopentadienones are widely used in rubber, resin, paint, pesticide, spices and other industries. [0003] 3,4-bis(3,4,5-trimethoxyphenyl)-2,5-diphenylcyclopentadienone is a cyclopentadienone compound in terms of its skeleton structure. The introduction of the phenyl substituent increases its molecular weight, increases its melting point, and becomes solid at ro...

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 Patents(China)
IPC IPC(8): C07C45/74C07C49/753
CPCC07C45/29C07C45/45C07C45/74C07C2601/10C07C49/84C07C49/753
Inventor 吴波于淼
Owner SHANDONG 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