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Preparation method of 2-methoxy-6-methyl benzoic acid

A technology of methyl benzoic acid and dimethyl anisole, applied in the directions of nitrile preparation, organic chemistry, etc., can solve the problems of serious environmental pollution, high cost, unsuitable for industrial production, etc., and achieves high reaction efficiency, low cost, Easy post-processing effects

Pending Publication Date: 2022-03-01
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In summary, the above three methods all use more than stoichiometric copper sulfate, which causes serious environmental pollution and high cost, and is not suitable for industrial production.

Method used

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  • Preparation method of 2-methoxy-6-methyl benzoic acid
  • Preparation method of 2-methoxy-6-methyl benzoic acid
  • Preparation method of 2-methoxy-6-methyl benzoic acid

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Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1: the synthesis of 2-methoxy-6-methylbenzoic acid

[0031] 2,3-Dimethylanisole (14.06g, 0.103mol), copper sulfate pentahydrate (0.26g, 0.001mol), phenanthroline (0.19g, 0.001mol) and potassium persulfate (55.68g, 0.206 mol) was sequentially added into a 1000mL three-necked flask equipped with mechanical stirring and a thermometer, 480mL of propionitrile and 320mL of water were added into the three-necked flask, stirred and heated to 70°C, and kept for 15 minutes for reaction. The reaction system was cooled to room temperature, then sulfamic acid (10.00 g, 0.103 mol) was added to the reaction system, after stirring evenly, sodium hypochlorite (7.67 g, 0.103 mol) was dissolved in 50 mL of water, and slowly added dropwise to the reaction system, After the dropwise addition was completed, the reaction was carried out at room temperature for 0.5h. After the reaction was completed, the mixture was separated by filtration, and then the reaction system was extracte...

Embodiment 2

[0034] Embodiment 2: the synthesis of 2-methoxy-6-methylbenzoic acid

[0035] 2,3-Dimethylanisole (14.06g, 0.103mol), copper sulfate pentahydrate (1.28g, 0.005mol), bipyridine (1.61g, 0.010mol) and potassium persulfate (69.61g, 0.258mol ) into a 1000mL three-necked flask equipped with a mechanical stirrer and a thermometer in sequence, 480mL of ethyl acetate and 320mL of water were added to the three-necked flask, stirred and heated to 80°C, and kept for 20 minutes for reaction. The reaction system was cooled to room temperature, then sulfamic acid (20.00 g, 0.206 mol) was added to the reaction system, after stirring evenly, sodium hypochlorite (15.33 g, 0.206 mol) was dissolved in 50 mL of water, and slowly added dropwise to the reaction system, After the dropwise addition was completed, the reaction was carried out at room temperature for 2h. After the reaction was completed, the mixture was separated by filtration, and then the reaction system was extracted three times wit...

Embodiment 3

[0036] Embodiment 3: the synthesis of 2-methoxy-6-methylbenzoic acid

[0037]2,3-Dimethylanisole (14.06g, 0.103mol), copper bromide (2.30g, 0.010mol), pyridine (0.81g, 0.010mol) and potassium persulfate (69.61g, 0.258mol) were sequentially Add to a 1000mL three-necked flask equipped with mechanical stirring and a thermometer, add 480mL of tetrahydrofuran and 320mL of water into the three-necked flask, stir and raise the temperature to 90°C, and keep the reaction for 40min. The reaction system was cooled to room temperature, then sulfamic acid (20.00 g, 0.206 mol) was added to the reaction system, after stirring evenly, sodium hypochlorite (15.33 g, 0.206 mol) was dissolved in 50 mL of water, and slowly added dropwise to the reaction system, After the dropwise addition was completed, the reaction was carried out at room temperature for 1.5h. After the reaction was completed, the mixture was separated by filtration, and then the reaction system was extracted three times with 50...

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Abstract

The invention discloses a preparation method of 2-methoxy-6-methyl benzoic acid, which comprises the following steps: adding raw materials 2, 3-dimethyl anisole, a copper salt, potassium persulfate, a ligand and a reaction solvent into a reaction container, stirring and heating to 50-100 DEG C, reacting for 0.25-10 hours, cooling the reaction system to room temperature, adding sulfamic acid and sodium hypochlorite, stirring and reacting for 0.5-10 hours, cooling to room temperature, filtering, washing, and drying to obtain the 2-methoxy-6-methyl benzoic acid. And carrying out post-treatment on the reaction liquid to obtain the product 2-methoxy-6-methyl benzoic acid, the method has the advantages of small amount of used copper salt, low cost, environmental friendliness, simple reaction process, convenience in post-treatment, high reaction efficiency and industrial application value.

Description

technical field [0001] The present invention relates to a new method for preparing 2-methoxy-6-methylbenzoic acid. Background technique [0002] 2-methoxyl-6-methylbenzoic acid is an important intermediate of the pesticide insecticide metrafenone, and the existing methods for preparing 2-methoxyl-6-methylbenzoic acid mainly include the following three types: [0003] Method one is as follows (references: Samir Kumar Mandal, Subhas Chandra Roy, Titanocene(III) chloride mediated radical-induced synthesis of 3,4-Dihydroisocoumarins: synthesis of hydrangenol, phyllodulcin, macrophyllol and hunberginol G, Tetrahedron, 2008: 11050-11057 ): With 2-hydroxyl-6-methylbenzaldehyde as raw material, add 1.2 equivalents of potassium carbonate and 1.5 equivalents of methyl iodide, take acetonitrile as solvent, react at reflux temperature, and react to obtain intermediate 2-methoxy-6- Tolylbenzaldehyde, then use 2-methoxy-6-methylbenzaldehyde as raw material, add silver oxide and sodium hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/08C07C65/21
CPCC07C51/08C07C65/21
Inventor 张国富叶家宏丁成荣吕井辉
Owner ZHEJIANG UNIV OF TECH