Method for synthesizing aromatic ketone compound

A technology for compounds and aromatic ketones, which is applied in the field of catalytic preparation of aromatic ketone compounds, can solve the problems of poor catalyst stability, serious environmental pollution and high corrosiveness, and achieves the effects of strong stability, high catalytic activity and simple process

Active Publication Date: 2014-09-17
大连海化医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to provide a deep eutectic method for F-C acylation to prepare aromatic ketones for the shortcomings of the current technology, such as high catalyst toxicity, high corrosiveness, serious

Method used

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  • Method for synthesizing aromatic ketone compound
  • Method for synthesizing aromatic ketone compound
  • Method for synthesizing aromatic ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Experimental method: Add 2mmol of 1,2,4-trimethoxybenzene into a 15mL round bottom flask, raise the temperature to 55°C, slowly add 2.2mmol of benzoyl chloride, and monitor the progress of the reaction by thin-layer chromatography. It was found that no product was formed, that is, in the absence of DES(ZnCl 2 / ChCl=2:1) ​​the reaction does not proceed in the presence of conditions.

[0033] Reaction equation:

[0034]

Embodiment 2

[0036] Experimental method: 1 equivalent (2mmol) of DES (ZnCl 2 / ChCl=2:1) ​​was added to a 15mL round bottom flask, then 1 equivalent (2 mmol) of 1,2,4-trimethoxybenzene was added, the temperature was raised to 55°C, and 1.1 equivalent (2.2 mmol) of benzene was slowly added Formyl chloride, the reaction was stopped after stirring for 10 minutes. After adding 5 mL of water and 5 mL of ethyl acetate to extract twice, the ethyl acetate layer was washed with saturated NaHCO 3 Wash once, then wash with anhydrous MgSO 4 After drying and distillation under reduced pressure, the obtained substance was subjected to column separation with a developing solvent of petroleum ether: ethyl acetate = 6:1. The yield of 2,4,5-trimethoxyphenylbenzophenone was 89.7%.

[0037] Reaction equation:

[0038]

Embodiment 3

[0040] Experimental method: the water layer in example 2 is distilled under reduced pressure, recyclable obtains DES (ZnCl 2 / ChCl=2:1). Using recovered DES(ZnCl 2 / ChCl=2:1) ​​Repeat the steps of Example 2. So repeated 4 times, it was found that DES(ZnCl 2 / ChCl=2:1) ​​the catalytic effect remains basically unchanged. The yields of the obtained products were: 89.4%, 89.2%, 88.5%, 87.7%.

[0041] Reaction equation:

[0042]

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Abstract

The invention relates to a method for synthesizing an aromatic ketone compound and particularly relates to DES (Deep Eutectic Solvents) catalyzed Friedel-Crafts (F-C) acylation reaction methods. The aromatic ketone compound is synthesized from an aromatic hydrocarbon compound and an acylating reagent through F-C acylation reaction, and a DES (wherein the ratio of ZnCl2/ChCl is 2: 1) serves as a catalyst during reaction. According to the method, the DES (wherein the ratio of ZnCl2/ChCl is 2:1) serves as the reaction catalyst while serving as a reaction solvent; the process is simple, the stability is strong, no volatilization exists, and the catalytic activity is high; during reaction aftertreatment, acid is not required to be added, so that the method is simple, convenient and environmental friendly.

Description

technical field [0001] The invention relates to a method for catalytically preparing aromatic ketones, more specifically, to a method for catalytically synthesizing aromatic ketones through Friedel-Crafts acylation using a deep eutectic solvent. Background technique [0002] Friedel-Crafts (F-C) acylation reaction is an important reaction for the preparation of aromatic ketones, and the obtained product aromatic ketones are important intermediates, which can be used to synthesize drugs (such as naproxen , dextromethorphan), dyes and agricultural chemicals, etc., because it has a wide range of application prospects, people have carried out in-depth research on its synthetic methods. [0003] F-C acylation reaction is an electrophilic substitution reaction between an aromatic compound and an acylating reagent. The acylating reagent is usually acid chloride, acid anhydride, or carboxylic acid, and the choice of catalyst is the core issue of this type of reaction. or Lewis acid...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/46C07D333/22
CPCC07B41/06C07C45/46C07D333/22C07C49/84
Inventor 王爱玲邢鹏飞郑学良李长平郑学仿
Owner 大连海化医药科技有限公司
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