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Novel method for synthesizing p-nitrobenzophenone

A technology for p-nitrobenzophenone and p-fluoronitrobenzene is applied in the field of nucleophilic acylation to synthesize p-nitrobenzophenone, and can solve the problems of difficulty in separation, recovery and reuse, large environmental pollution and poor stability. and other problems, to achieve the effect of simple operation and equipment requirements, high yield, and realization of recycling.

Inactive Publication Date: 2015-09-23
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the other hand, the current Friedel-Crafts acylation reaction mainly uses AlCl 3 Such as Lewis acid or concentrated sulfuric acid, etc. Acidic catalysts, these catalysts have certain shortcomings, such as poor stability, large dosage, serious corrosion, large environmental pollution, etc., especially the problem that it is difficult to separate, recycle and reuse

Method used

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  • Novel method for synthesizing p-nitrobenzophenone
  • Novel method for synthesizing p-nitrobenzophenone
  • Novel method for synthesizing p-nitrobenzophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Example 1: Add 0.05 mol of N-methylimidazole, 0.06 mol of n-chlorobutane and 10 mL of methanol into a 100 mL single-necked flask equipped with a reflux condenser. Raise the temperature to 70-80°C, and reflux for 24 hours. The solvent was evaporated under reduced pressure, and unreacted n-chlorobutane was absorbed with paraffin. The residue was washed twice with ethyl acetate, and the ethyl acetate was removed by rotary evaporation. Dried to obtain a yellow viscous ionic liquid (R=n-C 4 h 9 ).

Embodiment 2～5

[0018] Embodiment 2~5: change the n-butane chloride in embodiment 1 into n-octane chloride, n-dodecane chloride, n-octadecane chloride and benzyl chloride respectively, obtain imidazoles ionic liquid ( R=n-C 8 h 17 ,n-C 12 h 25 ,n-C 16 h 33 ,CH 2 Ph).

Embodiment 6

[0019] Embodiment 6: Add 3mmol p-fluoronitrobenzene, 3.6mmol benzaldehyde, 1mmol imidazoles ionic liquid (R=n-C 4 h 9 ) and 20 mL of solvent DMSO. After stirring for 5 min, 4 mmol potassium tert-butoxide was added to the three-necked flask. The reaction was stirred at 30 °C for 6 h. After the reaction was completed, ice water was added to the reaction solution. The organic matter was extracted twice with ethyl acetate, and the extracts were combined. Wash with water, wash with salt, dry and distill off the solvent under reduced pressure. The product was separated by column chromatography (petroleum ether: ethyl acetate = 25:1), and the crude product was recrystallized from ethanol to obtain colorless needle-like crystals. The conversion rate of p-fluoronitrobenzene was 85.3%, and the yield of p-nitrobenzophenone was 75.3%.

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Abstract

The invention relates to a novel method for synthesizing p-nitrobenzophenone. The method is characterized in that p-fluoronitrobenzene and benzaldehyde are adopted as raw materials; an imidazole ionic liquid is adopted as a catalyst precursor; and N-heterocyclic carbine is produced under the existence of alkali and is used for catalyzing a nucleophilic acylation reaction between the two substrates, such that p-nitrobenzophenone is produced. According to the invention, for a first time, ionic liquid is used as the nucleophilic acylation reaction catalytic precursor, such that catalyst recycling can be realized. Also, the synthesis method is implemented under a near room temperature, such that energy-consumption is low. The method also has the advantages of simple operation and high yield. When the ionic liquid is recycled 4 times, a p-nitrobenzophenone yield is still higher than 75%.

Description

technical field [0001] The present invention relates to a new method for synthesizing p-nitrobenzophenone, in particular to a kind of imidazole ionic liquid as the precursor of N-heterocyclic carbene (NHC) catalyst, which is synthesized by nucleophilic acylation reaction New approach to p-nitrobenzophenone. Background technique [0002] As we all know, aromatic ketones are an important class of fine chemicals and pharmaceutical intermediates, which are mainly synthesized by Friedel-Crafts acylation reaction (CN201410276567; CN201410031080; CN201310241154). The acylating reagents mainly include acid halides, acid anhydrides and carboxylic acids, and their activity decreases in turn. The Friedel-Crafts acylation reaction is an important class of aromatic electrophilic substitution reactions, so the greater the electron cloud density on the aromatic ring, the easier the reaction will be. If the aromatic ring contains -NO 2 、-SO 3 When electron-withdrawing groups such as H, ...

Claims

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Application Information

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IPC IPC(8): C07C205/45C07C201/12B01J31/02
CPCY02P20/584Y02P20/54
Inventor 于凤丽解从霞袁冰于世涛鲁玉倩
Owner QINGDAO UNIV OF SCI & TECH
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