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Synthesis method of 7-acryloyloxy-4-methylcoumarin

The technology of methyl coumarin and acryloyloxy group is applied in the synthesis field of coumarin derivatives, can solve the problems of long reaction time, large environmental pollution, low product yield and the like, and achieves short reaction time and green process. Environmentally friendly and high-yield effects

Inactive Publication Date: 2017-05-17
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the traditional synthetic method of 7-acryloyloxy-4-methylcoumarin, 7-hydroxy-4-methylcoumarin and acrylic acid are used in the presence of dicyclohexylcarbodiimide, 4-dimethylaminopyridine 7-acryloyloxy-4-methylcoumarin is synthesized by esterification reaction. This method has the disadvantages of complex catalyst, by-product formation, low product yield, long reaction time, and large environmental pollution. At the same time, it uses Volatile organic solvents such as dichloromethane, etc., these solvents are not only harmful to the environment, but also have certain toxicity

Method used

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  • Synthesis method of 7-acryloyloxy-4-methylcoumarin
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  • Synthesis method of 7-acryloyloxy-4-methylcoumarin

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Embodiment 1

[0039] Add 7-hydroxy-4-methylcoumarin (0.5285g, 3mmol), tetrahydrofuran (40mL), potassium hydroxide solution (10mL) with a concentration of 16.8g / L, polyethylene glycol (0.05g ), ultrasonically disperse for 10 minutes, and seal the tube with a rubber stopper after adding a magnetic stir bar. Thereafter, place the reaction tube in an ice bath at 0°C for strong magnetic stirring, and at the same time perform repeated freezing-vacuumizing-nitrogen filling to completely remove the oxygen inside the reaction tube and the solvent. After the system is stable and mixed evenly, use once Acryloyl chloride (0.73ml, 9mmol) was injected dropwise into the reaction tube with a neutral syringe, and magnetically stirred in an ice-water bath for 2 hours. After the reaction is over, drop the mixed solution into ice deionized water, and a white flocculent precipitate precipitates out. After filtering, wash it with a sodium hydroxide solution with a concentration of 30g / L, then dissolve the precip...

Embodiment 2

[0041] Add 7-hydroxy-4-methylcoumarin (0.5285g, 3mmol), tetrahydrofuran (40mL), potassium hydroxide solution (10mL) with a concentration of 16.8g / L, polyethylene glycol (0.05g ), ultrasonically disperse for 20 minutes, and seal the tube with a rubber stopper after adding a magnetic stir bar. Thereafter, place the reaction tube in an ice bath at 0°C for strong magnetic stirring, and at the same time perform repeated freezing-vacuumizing-nitrogen filling to completely remove the oxygen inside the reaction tube and the solvent. After the system is stable and mixed evenly, use once Acryloyl chloride (1.22ml, 15mmol) was injected dropwise into the reaction tube with a neutral syringe, and magnetically stirred in an ice-water bath for 2 hours. After the reaction is over, drop the mixed solution into ice deionized water, and a white flocculent precipitate precipitates out. After filtering, wash it with a sodium hydroxide solution with a concentration of 40g / L, then dissolve the preci...

Embodiment 3

[0043] Add 7-hydroxy-4-methylcoumarin (0.5285g, 3mmol), tetrahydrofuran (40mL), potassium hydroxide solution (10mL) with a concentration of 22.4g / L, polyethylene glycol (0.1g ), ultrasonically disperse for 30 minutes, and seal the tube with a rubber stopper after adding a magnetic stir bar. Thereafter, place the reaction tube in an ice bath at 0°C for strong magnetic stirring, and at the same time perform repeated freezing-vacuumizing-nitrogen filling to completely remove the oxygen inside the reaction tube and the solvent. After the system is stable and mixed evenly, use once Acryloyl chloride (1.62ml, 20mmol) was injected dropwise into the reaction tube with a neutral syringe, and magnetically stirred in an ice-water bath for 2 hours. After the reaction is over, drop the mixed solution into ice deionized water, and a white flocculent precipitate precipitates out. After filtering, wash it with a sodium hydroxide solution with a concentration of 50g / L, then dissolve the precip...

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Abstract

The invention discloses a synthesis method of 7-acryloyloxy-4-methylcoumarin. According to the method, 7-hydroxy-4- methylcoumarin and acryloyl chloride react in a protective atmosphere under the action of a potassium hydroxide / polyethylene glycol composite catalyst to obtain 7-acryloyloxy-4-methylcoumarin. Polyethylene glycol in the composite catalyst has good complexing ability on K<+>, hydrolysis of acryloyl chloride can be avoided by polyethylene glycol, and the transformation rate of acyl chloride substitution reaction is greatly improved. The method has the advantages of short reaction time, high yield and the like; the defects that more by-products exist, the reaction time is long, the purity is low and the like in a traditional esterification reaction method are overcome; the purification process of a product is environmentally friendly; the adaptability in industrial production is significantly improved; and the product can be applied to the field of stimulus-response of a high-molecular polymer as a photosensitive monomer, and has good development prospect.

Description

technical field [0001] The invention relates to a synthesis method of coumarin derivatives, in particular to a method for synthesizing 7-acryloyloxy-4-methyl in one step using 7-hydroxy-4-methylcoumarin and acryloyl chloride as reaction raw materials The method for coumarin (AOM) belongs to the field of synthesis of fine organic chemical intermediates. Background technique [0002] Coumarin is the mother nucleus of a large class of coumarin-like compounds that exist in the plant kingdom. Coumarin and its derivatives are widely distributed in the plant kingdom, especially in angiosperms, such as: Fabaceae, Compositae, Umbelliferae, Rutaceae, Daphneaceae, etc., because of their excellent anti-AIDS, Anti-tumor, anti-radiation and photodimerization properties, so it is widely used in biology, medicine, dyes, polymer science and other fields. In particular, by using its fast photoresponse performance to external light stimuli (such as ultraviolet, near-infrared, etc.), it is po...

Claims

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Application Information

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IPC IPC(8): C07D311/16B01J31/26
CPCC07D311/16B01J23/04B01J31/06B01J31/26B01J2231/49B01J35/19
Inventor 刘辉王锋邹应萍邹虎杨周晓爽
Owner CENT SOUTH UNIV
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