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Preparation method of 4,4'-di-trifluoromethyl benzil

A technology of fluoromethylbenzyl and trifluoromethylphenyl, which is applied in the field of organic compound synthesis, can solve the problems of low yield, complicated catalyst preparation, long reaction time and the like, and achieves high product yield and easy reaction process. Control, the effect of short reaction time

Inactive Publication Date: 2013-12-25
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method catalyst preparation is loaded down with trivial details, and reaction time is longer, and productive rate is low

Method used

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  • Preparation method of 4,4'-di-trifluoromethyl benzil
  • Preparation method of 4,4'-di-trifluoromethyl benzil
  • Preparation method of 4,4'-di-trifluoromethyl benzil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Preparation of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone

[0029] Under ice-water bath, add VB into the reactor successively 1 1.2g, 5.0mL distilled water, 15.0mL absolute ethanol and keep it for 15min, slowly add 3.3mol / L sodium hydroxide ethanol solution at 0~5℃ dropwise under stirring until the pH value of the solution is 8.0. Add 12.7g of p-trifluoromethylbenzaldehyde, adjust the pH value of the solution to 8.0 with 3.3mol / L sodium hydroxide ethanol solution at 0-5°C again, react at 60°C for 2h, cool in an ice-water bath, filter with suction, and filter the cake Wash with cold distilled water until the filtrate is neutral to give a white solid, which is recrystallized from ethanol to give 6.4 g of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone with a yield of 50.3% .

[0030] (2) Preparation of 4,4'-bistrifluoromethylbenzil

[0031] Add 6.4 g of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone, 3.0 g of ammonium nitrate, 1.0 g of anhydrous c...

Embodiment 2

[0037] (1) Preparation of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone

[0038] Under ice-water bath, add vitamin B to the reactor sequentially 1 2.9g, distilled water 10.0mL, absolute ethanol 32.0mL and keep it for 15min, slowly add 3.3mol / L sodium hydroxide ethanol solution at 0~5℃ dropwise under stirring until the pH value of the solution is 8.0. Add 25.5g of p-trifluoromethylbenzaldehyde, adjust the pH value of the solution to 8.0 with 3.3mol / L sodium hydroxide ethanol solution at 0-5°C again, react at 70°C for 3 hours, cool in an ice-water bath, filter with suction, and use for filter cake After washing with cold distilled water until the filtrate was neutral, a white solid was obtained, which was recrystallized from ethanol to obtain 13.7 g of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone with a yield of 53.7%.

[0039] (2) Preparation of 4,4'-bistrifluoromethylbenzil

[0040]Add 13.7g of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone, 8.0g of ammoniu...

Embodiment 3

[0042] (1) Preparation of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone

[0043] Under ice-water bath, add vitamin B to the reactor sequentially 1 1.2g, 5.0mL distilled water, 15.0mL absolute ethanol and keep it for 15min, slowly add 3.3mol / L sodium hydroxide ethanol solution at 0~5℃ dropwise under stirring until the pH value of the solution is 8.0. Add 12.7 g of p-trifluoromethylbenzaldehyde, adjust the pH value of the solution to 8.0 with 3.3 mol / L sodium hydroxide ethanol solution at 0-5°C again, react at 60-70°C for 4 hours, cool in an ice-water bath, and filter with suction. The filter cake was washed with cold distilled water until the filtrate was neutral to obtain a white solid, which was recrystallized from ethanol to obtain 6.6 g of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone with a yield of 51.7%.

[0044] (2) Preparation of 4,4'-bistrifluoromethylbenzil

[0045] Add 6.4 g of 1,2-bis(-4-trifluoromethylphenyl)-2-hydroxyethanone, 3.0 g of ammonium nit...

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Abstract

The invention relates to a preparation method of a 4,4'-di-trifluoromethyl benzil. The preparation method comprises the steps of: preparing 1,2-di(4-trifluoromethyl phenyl)-2-hydroxyl ketone through condensation reaction under alkaline condition by using p-trifluoromethyl benzaldehyde as a raw material and vitamin B1 (VB1) as a catalyst; in glacial acetic acid, oxidizing 1,2-di(4-trifluoromethyl phenyl)-2-hydroxyl ketone by using anhydrous cupric sulfate and ammonium nitrate as a co-oxidizing agent so as to obtain 4,4'-di-trifluoromethyl benzyl. The reaction time is short, the reaction condition is moderate, the reaction process is easy to control, and the yield of a product is high, therefore, the preparation method is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of 4,4'-bistrifluoromethylbenzil, which belongs to the technical field of organic compound synthesis. Background technique [0002] Benzil compounds have non-conjugated aromatic α, α′-dicarbonyl structures, exhibit special reactivity, and are important intermediates in organic synthesis and drug synthesis, especially in drug synthesis. Important intermediates of antiepileptic drugs. In addition, benzil compounds have special uses in the manufacture of insecticides, resin curing photosensitizers, food packaging and printing inks. In recent years, the synthesis and application of benzil compounds have become more and more research hotspots. [0003] Fluorine-containing organic compounds have many advantages due to the influence of fluorine atoms. The fluorine atom has a small radius and a large electronegativity. The bond energy of the C-F bond is much higher than that of the C-H bond, which increases the ...

Claims

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Application Information

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IPC IPC(8): C07C49/813C07C45/29
Inventor 吴波刘磊赵鹏超姜山于淼
Owner SHANDONG UNIV
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