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Method for synthesizing xanthoxylin WGX-50 and derivatives thereof in one pot

A technology of WGX-50 and xanthanin, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of poor control of yield and purity, environmental hazards, improper handling, etc.

Pending Publication Date: 2022-04-12
上海彤颜实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This route obtains the target product through a three-step reaction, and produces hydrogen chloride gas and sulfur dioxide gas. Improper handling will cause harm to the environment, and the yield and purity of the obtained product are not well controlled due to the reaction route.

Method used

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  • Method for synthesizing xanthoxylin WGX-50 and derivatives thereof in one pot
  • Method for synthesizing xanthoxylin WGX-50 and derivatives thereof in one pot
  • Method for synthesizing xanthoxylin WGX-50 and derivatives thereof in one pot

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment one, the preparation of catalyst system

[0036] The molecular sieve is activated at a high temperature of 140°C for 1-2 hours before use, and then the activated molecular sieve, catalyst and dehydrating agent are added to the reaction system before the reaction, and the catalytic system is obtained by replacing the inert gas.

Embodiment 2

[0037] Embodiment two, the preparation of xanthoxylin WGX-50 and derivative thereof

[0038] The chemical reaction formula is as follows:

[0039]

[0040] When substituent A is C 1 -C 3 For alkyl groups, take the synthesis of N-phenethyl cinnamic amide as an example.

[0041] Step 1-1, Weigh 5.00g (47.1mmol) of benzaldehyde and 50ml (293.3mmol) of n-butyl ether in a 100ml reaction bottle, install a condenser on the reaction bottle, and mix 6.69g (47.1mmol) of molecular sieve activated at 140°C with 6.69g (47.1mmol) ) phosphorus pentoxide and 1.09g (4.71mmol) zirconium chloride together form the catalyst system into the reaction flask, replace with inert gas nitrogen three times, discharge the air in the system, raise the temperature to 120 ° C, and then add 4.81g (47.1mmol) Acetic anhydride was slowly added to the system, reacted for 5 hours, and the acetic acid gas generated by the reaction was recovered through the condenser.

[0042] Step 1-2, remove the condenser o...

Embodiment 3

[0047] Embodiment three, the preparation of xanthoxylin WGX-50 and derivative thereof

[0048] The chemical reaction formula is as follows:

[0049]

[0050] When substituent A is selected from: -OCCH 3 , -OCOMe, C 1 -C 3 When alkoxy or phenyl, take the synthesis of N-(3,4-dimethoxyphenethyl)cinnamic amide as an example.

[0051] Step 1-1, Weigh 5.00g (47.1mmol) of benzaldehyde and 50ml (293.3mmol) of n-butyl ether in a 100ml reaction bottle, install a condenser on the reaction bottle, and mix 2.64g (47.1mmol) of molecular sieves activated at 140°C with 2.64g (47.1mmol) ) Calcium oxide and 1.09g (4.71mmol) zirconium chloride together form the catalytic system into the reaction flask, replace with inert gas nitrogen three times, discharge the air in the system, raise the temperature to 120 ° C, and then add 4.81g (47.1mmol) acetic anhydride Slowly add to the system, fully react for 6h, and the acetic acid gas generated is recovered through the condenser.

[0052] Step 1...

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Abstract

The invention discloses a method for one-pot synthesis of xanthoxylin WGX-50 and derivatives thereof, which is characterized in that the high-yield and high-purity xanthoxylin WGX-50 and derivatives thereof are synthesized by one-pot synthesis of aromatic aldehyde, acetic anhydride and aromatic amine in a stable catalytic system by controlling the adding time and adding modes of different substances.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for one-pot synthesis of xanthoxylin WGX-50 and derivatives thereof. Background technique [0002] The characteristic structure of Xanthoxylin WGX-50 and its derivatives is an acrylamide structure. Substances with this structure can be used in cosmetics to play anti-aging, antibacterial, regulating skin metabolism, and anti-hair loss effects. In addition, studies have shown that substances with this structure play an important role in nerve cell apoptosis, and can be used as drugs to prevent or treat some neurodegenerative diseases. [0003] At present, the synthesis of this kind of substance is mainly to obtain aromatic acrylic acid through Perkin reaction of aromatic aldehyde and acid anhydride, then carry out acyl chloride reaction to obtain aromatic acryloyl chloride, and then perform aminolysis reaction to obtain aromatic acrylamide. The reaction process i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/11C07C233/22C07C231/12
CPCY02P20/55
Inventor 张守兵琚建伟丁保安
Owner 上海彤颜实业有限公司
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