Method for synthesizing 4-hydroxy benzenepropionamido benzoic acid

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, pollution reduction, and labor intensity reduction Effect

Inactive Publication Date: 2015-03-18
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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  • Method for synthesizing 4-hydroxy benzenepropionamido benzoic acid
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  • Method for synthesizing 4-hydroxy benzenepropionamido benzoic acid

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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) into a single-neck bottle, and stir at 18°C ​​at room temperature. Thionyl chloride (2ml, 0.027mol) was added dropwise to the suspension and stirred at room temperature for about 3 hours. The system changed from slightly muddy to a clear yellow solution. Continue to add methyl anthranilate (2.7g, 0.018mol). ), after the dripping, a large amount of white solid precipitated, and then sodium carbonate (3g, 0.0283mol) was added, the system became very viscous, after 3 hours of reaction, TLC spot plate (take a little sample, add water and ethyl acetate, organic Layer point board, develop solvent ethyl acetate: petroleum ether=1:5 (V / V)), generate a main point. After 4 hours, the plate was turned on. The raw materials were reduced, but the solution was acidic. Add 1 g of sodium carbonate to continue the reaction. Extend the reaction time overnight (12 hours), TL...

Embodiment 2

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

Embodiment 3

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

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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 present invention relates to the field of cosmetics, in particular to a method for synthesizing dihydrooatyl anthranilic acid D. Background technique [0002] Dihydrooatylanthranilic acid D has anti-irritation and anti-itching functions. It is widely used in daily chemical products, such as baby diaper cream, shampoo, hair removal cream, etc. It is a substitute for oatanthramide and can significantly improve Clinical symptoms in patients with dry and itchy skin. [0003] The synthesis of dihydrooatylanthranilic acid D has only been reported in patent WO2005016870 until now: [0004] [0005] This method applies a typical amide condensation method, using CDI and pyridine p-toluenesulfonic acid salt, imidazole, pyridine and p-toluenesulfonic acid are not easy to recycle and reuse in the post-treatment process, causing the discharge of a large amount of organic wastewater and serious environmental pollution; The use of tetrahydrofuran requires anhydrous trea...

Claims

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Application Information

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Patent Type & Authority Applications(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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