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Preparation method of 2-(2-nitryl-4-methyl sulfuryl-benzoyl) cyclohexane-1,3-diketone

A benzoyl and methylsulfonyl technology is applied in the field of preparation of 2-(2-nitro-4-methylsulfonyl-benzoyl)cyclohexane-1,3-dione, and can solve the reaction steps Many problems, lack of competitiveness, immaturity, etc., to achieve the effect of simple operation and environmental friendliness

Active Publication Date: 2013-06-26
INSIGHT FINECHEM +1
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  • Abstract
  • Description
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Problems solved by technology

[0011] The second method: the used raw material price of sulfonyl chlorination method is easy to obtain, and the amount of three wastes is less in the production process, but there is no document at present with the report of directly synthesizing the target object with this route, can only refer to the relevant documents of step-by-step reaction and similar reaction , so the process is not mature enough, and there are more reaction steps, and there is still a lot of optimization and improvement work to be completed urgently
This route has a certain novelty, but the process needs to use expensive anhydrous bromine, and the cost is high. At present, it is only suitable for the preparation of a small amount of samples in the laboratory, and the large-scale industrial production is not competitive.

Method used

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  • Preparation method of 2-(2-nitryl-4-methyl sulfuryl-benzoyl) cyclohexane-1,3-diketone
  • Preparation method of 2-(2-nitryl-4-methyl sulfuryl-benzoyl) cyclohexane-1,3-diketone
  • Preparation method of 2-(2-nitryl-4-methyl sulfuryl-benzoyl) cyclohexane-1,3-diketone

Examples

Experimental program
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Embodiment 1

[0038] (1) Synthesis of 2-(2-nitro-4-methylsulfonyl-benzylhydroxy)cyclohexane-1,3-dione (MST01)

[0039] In a 2L four-necked flask, add 2-nitro-4-methylsulfonylbenzaldehyde (114.5g / 0.5mol), 1,3-cyclohexanedione (67.2g / 0.6mol) and 400ml toluene in sequence, stir and mix Control the temperature of the reaction system at 10~15℃, add N, N-dimethylbenzylamine (94.5g / 0.7mol) dropwise, after the dropwise addition, continue the heat preservation reaction for 1.5h, stop the reaction, use dilute sulfuric acid (wt 20 %) Adjust the system to neutral to obtain a mixed solution of intermediate MST01, which can be directly used in the next reaction.

[0040] (2) Synthesis of 2-(2-nitro-4-methylsulfonyl-benzoyl)cyclohexane-1,3-dione (MST)

[0041] Control the temperature of the MST01 mixture at 40~45℃, add 30% hydrogen peroxide (62.33g / 0.55mol), stir and mix well, add 120ml dilute sulfuric acid (wt 20%) dropwise, after the dropwise addition, continue to keep the temperature for 2h, stop heating Th...

Embodiment 2

[0044] (1) Synthesis of 2-(2-nitro-4-methylsulfonyl-benzylhydroxy)cyclohexane-1,3-dione (MST01)

[0045] In a 2L four-necked flask, add 2-nitro-4-methylsulfonylbenzaldehyde (114.5g / 0.5mol), 1,3-cyclohexanedione (67.2g / 0.6mol) and 400ml tetrahydrofuran in sequence, and stir to mix. Evenly, control the temperature of the reaction system at 35-40℃, add 400ml sodium hydroxide aqueous solution (wt 5%) dropwise, after the dropwise addition, continue to keep the reaction for 40 minutes, stop the reaction, adjust the system to neutral with dilute sulfuric acid (wt 20%) , The mixed solution of intermediate MST01 can be directly used in the next reaction.

[0046] (2) Synthesis of 2-(2-nitro-4-methylsulfonyl-benzoyl)cyclohexane-1,3-dione (MST)

[0047] Control the temperature of the MST01 mixture at 55~60℃, add peroxyacetic acid (41.5g / 0.55mol) dropwise, stir and mix, after the dropwise addition, continue to keep the reaction for 1h, stop heating, and cool the reaction solution to 0 with an i...

Embodiment 3

[0050] (1) Synthesis of 2-(2-nitro-4-methylsulfonyl-benzylhydroxy)cyclohexane-1,3-dione (MST01)

[0051] In a 2L four-necked flask, add 2-nitro-4-methylsulfonylbenzaldehyde (114.5g / 0.5mol), 1,3-cyclohexanedione (67.2g / 0.6mol) and 400ml sulfolane, stir and mix Control the temperature of the reaction system at 10-15°C, add 300ml of sodium carbonate aqueous solution (wt 15%) dropwise, after the dropwise addition, continue the heat preservation reaction for 2h, stop the reaction, adjust the system to neutral with dilute sulfuric acid (wt 20%), The mixed solution of intermediate MST01 can be directly used in the next reaction.

[0052] (2) Synthesis of 2-(2-nitro-4-methylsulfonyl-benzoyl)cyclohexane-1,3-dione (MST)

[0053] At room temperature, add ceric ammonium nitrate (164.4g / 0.3mol) to the mixture of MST01, stir and mix, add 50ml dilute sulfuric acid (wt 20%) dropwise, after the dropwise addition, continue to react at room temperature for 3h, stop heating, the reaction solution Use ...

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Abstract

The invention relates to a preparation method of 2-(2-nitryl-4-methyl sulfuryl-benzoyl) cyclohexane-1,3-diketone (methyl mesotrione, mesotrione). The preparation method adopting 2-nitryl-4-methyl sulfuryl benzaldehyde and 1,3-cyclohexanedione as the materials comprises the following steps of: carrying out the reactions including nucleophilic addition, oxidation and the like to prepare the high-purity 2-(2-nitryl-4-methyl sulfuryl-benzoyl) cyclohexane-1,3-diketone. The preparation method disclosed by the invention is short in route; all steps are free of severe conditions, simple to operate, environment-friendly, remarkable in innovative significance and economic value and extensive in industrial production prospect.

Description

Technical field [0001] The invention relates to a preparation method and production process of a novel pesticide herbicide 2-(2-nitro-4-methylsulfonyl-benzoyl)cyclohexane-1,3-dione (MST). The method of the invention It uses 2-nitro-4-methylsulfone-benzaldehyde and 1,3-cyclohexanedione as raw materials to prepare 2-(2-nitro-4-methylsulfone through nucleophilic addition and oxidation reactions Benzyl-benzoyl)cyclohexane-1,3-dione, the product purity is greater than 99%, and the total yield is more than 69%. The preparation method of the present invention has the characteristics of short route, mild reaction conditions, smooth operation, and environmental protection. It is expected to be applied to actual production. . Background technique [0002] 2-(2-Nitro-4-methylsulfonyl-benzoyl)cyclohexane-1,3-dione (MST), also known as mesotrione and mesotrione, is produced by Swiss Syngenta A triketone herbicide was developed, which is an inhibitor of p-hydroxypyruvate dioxygenase (HPPD) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07C315/04
Inventor 李永芳黄碧波凌云殷巍
Owner INSIGHT FINECHEM
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