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A kind of preparation method of polysubstituted benzoate

A benzoate and multi-substituted technology is applied in the field of preparation of multi-substituted benzoates, and can solve the problems of low yield, cumbersome synthesis route, difficult post-processing and the like

Active Publication Date: 2021-05-14
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have problems such as cumbersome synthetic routes, low yields, and difficult post-processing.

Method used

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  • A kind of preparation method of polysubstituted benzoate
  • A kind of preparation method of polysubstituted benzoate
  • A kind of preparation method of polysubstituted benzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 3mL of toluene to a 10mL round bottom flask, then add 1mmol ethyl acetoacetate and 1mmol toluene and mix uniformly to obtain a mixed solution. Add 5% cuprous chloride of the total mass of the mixed solution as a catalyst to form a reaction system. The reaction system was heated to 90 degrees Celsius, and the reaction was stirred for 16 hours under the condition that the temperature of the reaction system was kept at 90 degrees Celsius. After the reaction, the reaction product obtained was extracted three times with ethyl acetate and water 30mL (volume ratio 2:1), and a certain amount of anhydrous magnesium sulfate was added to the obtained upper organic phase to stand overnight for drying, and the solvent toluene was evaporated under reduced pressure. The crude product was obtained, and the crude product was subjected to flash silica gel column chromatography to obtain the multi-substituted benzoate compound 3a.

Embodiment 2

[0031] Add 3mL of toluene to a 10mL round bottom flask, then add 3mmol methyl acetoacetate and 1mmol toluene and mix well to obtain a mixed solution. 7% cuprous iodide of the total mass of the mixed solution was added as a catalyst to form a reaction system. The reaction system was heated to 100 degrees Celsius, and the reaction was stirred for 20 h under the condition that the temperature of the reaction system was kept at 100 degrees Celsius. After the reaction, the reaction product obtained was extracted three times with ethyl acetate and water 30mL (volume ratio 2:1), and a certain amount of anhydrous magnesium sulfate was added to the obtained upper organic phase to stand overnight for drying, and the solvent toluene was evaporated under reduced pressure. The crude product was obtained, and the crude product was subjected to flash silica gel column chromatography to obtain the multi-substituted benzoate compound 3b.

Embodiment 3

[0033] Add 3mL of toluene to a 10mL round bottom flask, then add 5mmol isopropyl acetoacetate and 1mmol toluene and mix well to obtain a mixed solution. 10% cuprous bromide of the total mass of the mixed solution is added as a catalyst to form a reaction system. The reaction system was heated to 110 degrees Celsius, and the reaction was stirred for 24 hours under the condition that the temperature of the reaction system was kept at 110 degrees Celsius. After the reaction, the reaction product obtained was extracted three times with ethyl acetate and water 30mL (volume ratio 2:1), and a certain amount of anhydrous magnesium sulfate was added to the obtained upper organic phase to stand overnight for drying, and the solvent toluene was evaporated under reduced pressure. The crude product was obtained, and the crude product was subjected to flash silica gel column chromatography to obtain the multi-substituted benzoate compound 3c.

[0034] The structural formulas of the above-m...

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Abstract

The invention relates to a preparation method of multi-substituted benzoic acid esters. Acetoacetate derivatives and toluene are dissolved in a solvent to obtain a mixed solution, a copper catalyst is added to obtain a reaction system, and then the reaction system is heated to 90-110 degrees Celsius, stirred and reacted to obtain a reaction product, the obtained reaction product was extracted, dried, and the solvent was evaporated under reduced pressure to obtain a crude product, and the crude product was purified to obtain a polysubstituted benzoate compound. The method can directly synthesize multi-substituted benzoate esters from simple acyclic precursor acetoacetate derivatives and toluene in one step. The synthetic route has simple steps, high atom economy, and the target product is easy to separate and has high yield.

Description

technical field [0001] The invention relates to a preparation method of benzoic acid ester compounds, in particular to a preparation method of multi-substituted benzoic acid esters. [0002] technical background [0003] Benzoic acid ester compounds are an important intermediate of chemical products, which are widely used in the production fields of fine chemicals, agricultural chemicals, pharmaceuticals, biological preparations and functional foods. For example, ethyl p-nitrobenzoate is a synthetic benzoate Caine, tetracaine hydrochloride, an important raw material for ultraviolet absorbers; ethyl 3,5-dimethylbenzoate can be used as a release agent and a coating additive, etc. [0004] At present, the methods for synthesizing multi-substituted benzoic acid esters mainly include direct or indirect esterification of substituted benzoic acid compounds, and transesterification of substituted benzoic acid compounds with other compounds. However, these methods have problems such ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/347C07C69/76
CPCC07C67/347C07C69/76
Inventor 黄国保韦庆敏罗志辉罗金荣韦贤生
Owner YULIN NORMAL UNIVERSITY
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