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Green preparation process of 2-methyl-3-methoxybenzoyl chloride

A technology of methoxybenzoyl chloride and methoxybenzoyl chloride solution is applied in the field of synthesis of organic pesticide intermediates, and can solve the problem that 2-methyl-3-methoxybenzoic acid is not easily available, environment and worker health Great harm to the health of workers in the working environment, etc., to avoid the harm to the working environment and the health of workers, good economic and social benefits, and low toxicity

Active Publication Date: 2021-07-13
JIANGSU YONGAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the above-mentioned technical solution has the following disadvantages: 1) 2-methyl-3-methoxybenzoic acid is not easy to obtain, usually by 3-nitro-2-methylbenzoic acid, through reduction, diazotization, methoxy made
Moreover, on the one hand, solid dust is formed during the solid drying process, which is harmful to the working environment and workers' health; on the other hand, during neutralization, part of the salt is wrapped in 2-methyl-3-methoxybenzoic acid, which is difficult to remove , requiring a lot of washing
2) Acyl chloride or acylation steps are usually carried out in highly toxic dichloroethane (such as CN 106699596 A, CN 104803879 A, ​​CN 102584573 A, etc.), which is very harmful to the environment and workers’ health, and is not conducive to green production

Method used

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  • Green preparation process of 2-methyl-3-methoxybenzoyl chloride
  • Green preparation process of 2-methyl-3-methoxybenzoyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Hydrolysis: Add methyl 2-methyl-3-methoxybenzoate (80 g, 0.44 mol) and water (50 g) into the reaction kettle, raise the temperature to 90-100°C, add liquid caustic soda (59.8 g , 0.45 mol, 1.01 eq., concentration: 30%) solution, dropwise time 0.2h, after addition, the external temperature rises to 120-130 ℃, methanol is distilled out while reacting (distillate: 16.1 g, water content: 17.3 %);

[0038] (2) Neutralization: When the reaction is completed, cool down to 50-55°C, add 147 g of ethyl acetate, and add 107 g of 20% sulfuric acid dropwise under heat preservation, and control the dropping time for 0.1-1.0 h;

[0039] After the addition is completed, keep the temperature at 55-60°C for standing and stratification; the organic layer is to be washed with water, and the water layer is collected (about 214 g), cooled to 0-5°C for crystallization, and filtered to obtain about 47 g of sodium sulfate decahydrate, and 166 g of the filtrate ;

[0040] Add 50 g of water...

Embodiment 2

[0044](1) Hydrolysis: Add methyl 2-methyl-3-methoxybenzoate (160 g, 0.89 mol) and water (100 g) into the reaction kettle, raise the temperature to 90-100°C, add liquid caustic soda (120.0 g , 0.91 mol, 1.03 eq., concentration: 30.5%) solution, dropwise time 0.25 h, after addition, keep warm at 100-110°C for reaction, and distill methanol at the same time (distillate: 45.9 g, water content: 50%);

[0045] (2) When the reaction is completed, cool down to 75-80°C, add 600 g of isopropyl acetate, and add 140 g of 30% sulfuric acid dropwise under heat preservation, and control the dropping time for 0.1-1.0 h;

[0046] After the addition, keep the temperature at 55-60°C for standing and stratify; the organic layer is to be washed with water, and the water layer is collected (about 340 g), cooled to 5-10°C for crystallization, and filtered to obtain about 98 g of sodium sulfate decahydrate and 240 g of the filtrate ;

[0047] Add 100 g of water to the organic layer, keep warm at 50-...

Embodiment 3

[0051] (1) Hydrolysis: Add methyl 2-methyl-3-methoxybenzoate (100 g, 0.55 mol) and water (72 g) into the reaction kettle, raise the temperature to 90-100°C, add potassium hydroxide (109.0 g, 0.58mol, 1.05 eq., concentration: 30.0%) solution, dropwise addition time 0.33 h, after addition, keep warm at external temperature for 110-120 to react, and distill methanol at the same time (distillate: 20 g, water content: 34% );

[0052] (2) When the reaction is completed, cool down to 75-80°C, add 460 g of methyl isobutyl ketone, and add 86.7 g of 30% sulfuric acid dropwise under heat preservation, and control the dropping time for 0.5-1.0 h;

[0053] After the addition, keep the temperature at 50-60°C for standing and stratify; the organic layer is to be washed with water, and the water layer is collected (about 256 g), cooled to 0-5°C for crystallization, and filtered to obtain about 31 g of potassium sulfate and 226 g of the filtrate;

[0054] Add 70 g of water to the organic laye...

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Abstract

The invention discloses a green preparation process of 2-methyl-3-methoxybenzoyl chloride. The green preparation process comprises the following steps: heating and hydrolyzing methyl 2-methyl-3-methoxybenzoate in an alkaline aqueous solution, and distilling off generated methanol while a hydrolysis reaction is carried out; adding an organic solvent into hydrolyzed reaction liquid under the condition of heat preservation for dissolving, and adding an acidic aqueous solution for neutralizing; conducting neutralizing, then preserving heat and conducting layering to obtain a water layer and an organic layer, and washing the organic layer with water; heating the washed organic layer for azeotropic water removal; and adding a catalyst into the organic layer after azeotropic dehydration, carrying out heating, dropwise adding an acylating chlorination reagent, and carrying out a heat-preserved reaction to obtain the 2-methyl-3-methoxybenzoyl chloride. In a neutralization process after hydrolysis is completed, the organic solvent is added, and the product 2-methyl-3-methoxybenzoic acid is transferred into the organic solvent and is transferred to a subsequent reaction in a solution state, so water consumption for post-treatment is reduced, and meanwhile, harm to a working environment and the health of workers in the solid dust drying and feeding process is avoided.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic pesticide intermediates, and relates to the preparation process of methoxyfenozide intermediate 2-methyl-3-methoxybenzoyl chloride, specifically a kind of 2-methyl-3-methoxy Green preparation process of benzoyl chloride. Background technique [0002] Methoxyfenozide is the second-generation dihydrazide insect growth regulator, which was discovered by American Rohm-Haas (now Dow AgroSciences) company in 1990. At present, this product is produced by Dow AgroSciences and is sold in the world. Sales everywhere. The product has highly selective insecticidal activity against Lepidoptera pests, has no osmotic effect and phloem systemic activity, and is mainly effective through gastric toxicity. It also has certain contact and ovicidal activities. Methoxyfenozide, like other bishydrazide insecticides such as cyclofenozide, chlorfenozide and tebufenozide, is also an ecdysone agonist, which c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/60C07C51/09C07C51/41C07C51/42C07C51/46C07C51/48C07C65/21
CPCC07C51/60C07C51/09C07C51/412C07C51/42C07C51/46C07C51/48C07C65/21
Inventor 耿敬坤方浙能王晓军季品俊张如金姚林希
Owner JIANGSU YONGAN CHEM CO LTD
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