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A kind of dihydroovenalyl anthranilic acid D synthetic method

A technology of avenyl o-aminobenzoic acid, which is applied in chemical instruments and methods, preparation of carboxylic acid amides, preparation of organic compounds, etc., can solve the problems of emission and high production cost, and achieve emission avoidance, high controllability, and lightening pollution effect

Inactive Publication Date: 2017-02-01
SHANGHAI YIMING CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Aiming at the defects of organic matter discharge and high production cost in the synthesis methods of dihydroovenlyl anthranilic acid D in the prior art, the present invention provides a synthesis method of dihydroavenyl anthranilic acid D

Method used

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  • A kind of dihydroovenalyl anthranilic acid D synthetic method
  • A kind of dihydroovenalyl anthranilic acid D synthetic method
  • A kind of dihydroovenalyl anthranilic acid D synthetic method

Examples

Experimental program
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Effect test

Embodiment 1

[0032]

[0033] Add p-hydroxyphenylpropionic acid (3 g, 0.018 mol), DMF (0.25 ml, 0.0036 mol) and dichloromethane (100 ml) respectively into a single-necked bottle, and stir at room temperature at 18°C. Thionyl chloride (2ml, 0.027mol) was added dropwise to the suspension, stirred at room temperature for about 3 hours, the system gradually changed from slightly cloudy to a clear yellow solution, and methyl anthranilate (2.7g, 0.018mol) was continued to be added dropwise. ), after dropping, a large amount of white solids were precipitated, then sodium carbonate (3g, 0.0283mol) was added, and the system became very viscous. After 3 hours of reaction, TLC spotting (take a little sample, add water and ethyl acetate, organic Layer spot plate, developer ethyl acetate:petroleum ether=1:5 (V / V)), generate a principal point. After 4 hours, the board was tapped, the raw materials decreased, but the solution was acidic, and 1 gram of sodium carbonate was added to continue the reaction...

Embodiment 2

[0036] Add p-hydroxyphenylpropionic acid (4.58 g, 0.03 mol), DMF (0.4 ml, 0.003 mol) and dichloromethane (50 ml) respectively into a single-necked bottle, stir at room temperature or in a cold water bath (10°C). Thionyl chloride (3.6ml, 0.05mol) was added dropwise to the suspension, and stirred at room temperature for about 12 hours. The system gradually changed from a slightly turbid to a clear yellow solution, and methyl anthranilate (4.53g, 0.03mol) was added dropwise. ), after dropping, a large amount of white solids were precipitated, and sodium hydroxide (5.28g, 0.132mol) was added in batches. After 12 hours of reaction, the pH value was weakly alkaline, and dichloromethane was recovered by rotary evaporation to obtain solids, and water was added Add 30ml of methanol and 30ml of sodium hydroxide solution (2.14g, 0.066mol) with a concentration of 10mol / l, keep the pH value of the liquid in the one-necked bottle at 12, stir at room temperature for about 2 hours, the system ...

Embodiment 3

[0038]Add p-hydroxyphenylpropionic acid (3.0 g, 0.018 mol), DMF (0.25 ml, 0.0036 mol) and dichloromethane (50 ml) respectively into a single-necked bottle, and stir at 18°C. Add thionyl chloride (2ml, 0.027mol) dropwise to the suspension, stir at room temperature for about 0.5 hours, the system gradually changes from slightly turbid to a clear yellow solution, add methyl anthranilate (2.7g, 0.018mol) dropwise After dropping, a large amount of white solids precipitated, and disodium hydrogen phosphate trihydrate (4.93g, 0.0823mol) was added in batches, and after 12 hours of reaction, dichloromethane was recovered by rotary evaporation to obtain a solid, and 30 ml of water and ethanol were added , and add sodium hydroxide solution (2.14g, 0.066mol) with a concentration of 10mol / l, keep the pH value of the liquid in the one-mouth bottle at 12, stir at room temperature for about 24 hours, the system is milky white, add concentrated hydrochloric acid to adjust the pH value to 6 , a...

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Abstract

The invention provides a method for synthesizing 4-hydroxy benzenepropionamido benzoic acid. The method comprises the following steps: carrying out a thermal insulation reaction between p-hydroxybenzene propanoic acid and thionyl chloride in a cold bath at the temperature of 5-18 DEG C for 0.5-24 hours by taking a chlorinating reagent as a solvent; dripping methyl o-aminobenzoate, adding inorganic bases in batches, and stirring at the temperature of 8-35 DEG C for 8-48 hours until p-hydroxybenzene propanoic acid disappears, wherein the molar ratio of p-hydroxybenzene propanoic acid to methyl o-aminobenzoate to thionyl chloride to inorganic bases is 1 to 1 to 1-2 to 1-6; adding a concentrated solution of sodium hydroxide, recovering dichloromethane, adding an alcoholic solution, hydrolyzing for 2-48 hours at the hydrolysis temperature of 18-60 DEG C, and controlling the pH value to be 10-14; stopping the reaction after the hydrolysis is complete, cooling to room temperature, filtering out insoluble substances, regulating the pH value to be 4-7 by using hydrochloric acid or phosphoric acid, separating out white solids, filtering to collect the white solids, washing, and drying, thereby obtaining the product. According to the method disclosed by the invention, the yield can be improved, and the environmental pollution is reduced.

Description

technical field [0001] The invention relates to the field of cosmetics, in particular to a method for synthesizing dihydroavenyl anthranilic acid D. Background technique [0002] Dihydrooatyl anthranilic acid D has the functions of anti-irritation and anti-itching. It is widely used in daily chemical products, such as baby tummy cream, shampoo, hair removal cream, etc. It is a substitute for oat anthramid, which can significantly improve Clinical symptoms in a patient with dry itchy skin. [0003] The synthesis of dihydroovenalyl anthranilic acid D has only had the patent WO2005016870 so far to report its synthesis method: [0004] [0005] This method uses a typical amide condensation method, using CDI and pyridine p-toluenesulfonate. During the post-treatment process, imidazole, pyridine and p-toluenesulfonic acid are not easy to recycle and reuse, resulting in the discharge of a large amount of organic wastewater and serious environmental pollution; The use of tetrah...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/38C07C231/12
Inventor 苏东亮宫风华宫风杰
Owner SHANGHAI YIMING CHEM TECH CO LTD
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