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A kind of preparation method of 3,4-bis(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentadienone

A technology of diphenylcyclopentadienone and trifluorophenyl, which is applied in the field of organic compound synthesis, can solve the problems of increasing the difficulty of steric hindrance synthesis reaction, unfavorable industrial production, and no literature reports, etc. Safe and reliable, easy to separate and purify, and short reaction time

Inactive Publication Date: 2016-08-24
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is simple to operate and the conditions are easy to control, but the reaction time is too long, which is not conducive to industrial production
And for the preparation method of 3,4-bis(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentadienone that contains more fluorine atoms, there is no bibliographical information at present
The increase in the number of fluorine atoms improves the reactivity of nucleophilic addition, but at the same time increases the steric hindrance and increases the difficulty of the synthetic reaction.

Method used

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  • A kind of preparation method of 3,4-bis(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentadienone
  • A kind of preparation method of 3,4-bis(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentadienone
  • A kind of preparation method of 3,4-bis(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentadienone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Preparation of 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethanone

[0034] Under ice-water bath, add 1.8gVB successively to the reactor 1 , 5.0mL of distilled water, 15.0mL of absolute ethanol, and keep it for 10min, then add 11.0mL of 3,4,5-trifluorobenzaldehyde, slowly add dropwise 3.0mol / L sodium hydroxide ethanol solution at 3°C ​​to the solution with stirring The pH value was 9. After reacting for 45 minutes, it was heated to 60°C and reacted for another 90 minutes. Cool to room temperature, filter with suction, wash the filter cake three times with distilled water, and the filtrate is neutral, then recrystallize with ethanol to obtain 10.3g of 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethyl Ketone white crystals, m.p: 76-78°C (literature value: 75-77°C), yield 68.0%.

[0035] (2) Preparation of 3,4,5-ditrifluorobenzil

[0036]Add 10.3g 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethanone, 10.0g ammonium nitrate, 0.4g anhydrous copper sulfate, 25.0mL glacial acetic ...

Embodiment 2

[0044] (1) Preparation of 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethanone

[0045] Under the ice-water bath, add 3.6gVB successively to the reactor 1 , 10.0mL distilled water, 30.0mL absolute ethanol, and keep it for 20min, then add 22.0mL 3,4,5-trifluorobenzaldehyde, slowly add 3.0mol / L sodium hydroxide ethanol solution at 0°C dropwise under stirring to the solution The pH value was 9. After reacting for 45 minutes, it was heated to 70°C and reacted for another 2 hours. Cool to room temperature, filter with suction, wash the filter cake three times with distilled water, and the filtrate is neutral, then recrystallize with ethanol to obtain 21.8 g of 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethyl Ketone white crystals, m.p: 74-76°C, yield 71.8%.

[0046] (2) Preparation of 3,4,5-ditrifluorobenzil

[0047] Add 21.8g 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethanone, 20.0g ammonium nitrate, 0.8g anhydrous copper sulfate, 50.0mL glacial acetic acid, 20.0mL water, stirred and w...

Embodiment 3

[0051] (1) Preparation of 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethanone

[0052] Under ice-water bath, add 1.8gVB successively to the reactor 1 , 5.0mL distilled water, 15.0mL absolute ethanol, and keep it for 10min, then add 11.0mL 3,4,5-trifluorobenzaldehyde, slowly add 3.0mol / L sodium hydroxide ethanol solution at 5°C dropwise under stirring to the pH of the solution The value is 10. After reacting for 50 minutes, heat to 65° C. and react for another 3 hours. Cool to room temperature, filter with suction, wash the filter cake three times with distilled water, and the filtrate is neutral, then recrystallize with ethanol to obtain 10.6g of 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethyl Ketone white crystals, m.p: 76-79°C, yield 70.2%.

[0053] (2) Preparation of 3,4,5-ditrifluorobenzil

[0054] Add 10.6g 1,2-bis(3,4,5-trifluorophenyl)-2-hydroxyethanone, 10.0g ammonium nitrate, 0.4g anhydrous copper sulfate, 25.0mL glacial acetic acid, 10.0mL water, stirred and heated to...

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Abstract

The invention discloses a preparation method of 3,4-di(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentyldienone, which comprises the following steps: by using 3,4,5-trifluorobenzaldehyde as an raw material, vitamin B1 (VB1) as a catalyst and water and ethanol as a mixed solvent, carrying out condensation reaction under alkaline conditions to obtain 1,2-di(3,4,5-trifluorophenyl)-2-hydroxyethyl ketone; by using anhydrous cupric sulfate and ammonium nitrate as a co-oxidant, oxidating the 1,2-di(3,4,5-trifluorophenyl)-2-hydroxyethyl-one in glacial acetic acid to obtain 3,4,5-ditrifluorophenylbenzil; and finally, reacting the 3,4,5-ditrifluorophenylbenzil and dibenzyl ketone in hot ethanol under alkaline conditions to synthesize the 3,4-di(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentyldienone. The method has the advantages of cheap and accessible reaction raw materials, simple synthesis steps, short reaction time, mild reaction conditions and controllable reaction process, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 3,4-bis(3,4,5-trifluorophenyl)-2,5-diphenylcyclopentadienone, belonging to the technical field of organic compound synthesis. Background technique [0002] In recent years, cyclopentadienone compounds, as important organic chemical raw materials and reaction intermediates, have been paid more and more attention to their synthesis and application. Using cyclopentadienone derivatives as raw materials, many useful cyclic compounds and polymers can be synthesized. One of the uses of cyclopentadienone derivatives is to use them as diene reagents in the Diels-Alder reaction, and to react with vinyl-containing organosilicon monomers or polymers at high temperatures to obtain polyphenylphenyl organic compounds. Silicon compounds, as heat stabilizers and crosslinking agents for silicone rubber, can improve the thermal aging stability and mechanical strength of silicone elastomers. Cyclopentadienone derivatives ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/697C07C45/45
CPCC07C45/29C07C45/45C07C45/72C07C2601/10C07C49/697C07C49/813C07C49/83
Inventor 吴波牛娜于淼王欢贺欣欣
Owner SHANDONG UNIV
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