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Methyl 3-(cyanomethyl)benzoate synthetic method

A technology of methyl m-cyanomethyl benzoate and methyl cyanomethyl benzoate is applied in the field of synthesis of methyl m-cyanomethyl benzoate, and can solve the complex production process of methyl m-cyanomethyl benzoate and the high yield. low cost, high cost, to achieve the effect of environmental friendliness, high yield and low cost

Inactive Publication Date: 2015-12-09
WUHAN INSTITUTE OF TECHNOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Ketoprofen is an excellent anti-inflammatory analgesic, and it is an economical and environmentally friendly route to synthesize ketoprofen with methyl m-cyanomethyl benzoate as a starting material, but traditional m-cyanomethyl benzoate The production process of methyl formate is complicated, the cost is high, and the yield is low

Method used

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  • Methyl 3-(cyanomethyl)benzoate synthetic method
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  • Methyl 3-(cyanomethyl)benzoate synthetic method

Examples

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Embodiment 1

[0024] Such as figure 1 , m-cyanomethylbenzoic acid methyl ester synthetic method, take m-toluic acid as starting raw material, and its synthetic route is as follows:

[0025] The specific steps are as follows:

[0026] a): Pump 400 parts of m-toluic acid (I) into the chlorination kettle, add 410 parts of thionyl chloride, and make m-toluoyl chloride (II) by acylation reaction at 70°C. The rate is 90-97%;

[0027] b): Pump m-toluoyl chloride (II) into the chlorination kettle, and feed liquid chlorine with 4.6% weight of m-toluoyl chloride at 125°C to partially convert the acylate into chloride (Ⅲ ), distilling and recovering m-toluoyl chloride that did not participate in the reaction to the chlorination kettle for chlorination again until finally obtaining high-quality m-chloromethylbenzoyl chloride (Ⅲ);

[0028] c): Chloride (Ⅲ) is pumped into the esterification tank, and 80 parts of anhydrous methanol is added dropwise, and the esterification reaction is carried out at 40...

Embodiment 2

[0033] Such as figure 1 , m-cyanomethylbenzoic acid methyl ester synthetic method, take m-toluic acid as starting raw material, and its synthetic route is as follows:

[0034] The specific steps are as follows:

[0035] a): Take 400 parts of m-toluic acid (I) into the chlorination kettle, add 370 parts of thionyl chloride, and make m-toluoyl chloride (II) by acylation at 80°C. The rate is 90-97%;

[0036] b): Pump m-toluoyl chloride (II) into the chlorination kettle, and feed liquid chlorine with 13.8% weight of m-toluoyl chloride at 145°C to partially convert the acylate into chloride (Ⅲ ), distilling and recovering m-toluoyl chloride that did not participate in the reaction to the chlorination kettle for chlorination again until finally obtaining high-quality m-chloromethylbenzoyl chloride (Ⅲ);

[0037] c): Chloride (Ⅲ) is pumped into the esterification kettle, and 80 parts of anhydrous methanol is added dropwise, and the esterification reaction is carried out at 60°C to ...

Embodiment 3

[0041] Such as figure 1 , m-cyanomethylbenzoic acid methyl ester synthetic method, take m-toluic acid as starting raw material, and its synthetic route is as follows:

[0042] The specific steps are as follows:

[0043] a): Take 400 parts of m-toluic acid (I) into the chlorination kettle, add 380 parts of thionyl chloride, and make m-toluoyl chloride (II) by acylation at 60°C. The rate is 90-97%;

[0044] b): Pump m-toluoyl chloride (II) into the chlorination kettle, and feed liquid chlorine with 17.8% weight of m-toluoyl chloride at 170°C to partially convert the acylate into chloride (Ⅲ ), distill and recover the m-toluoyl chloride that did not participate in the reaction, and then chlorinate it again in the chlorination kettle until finally high-quality m-chloromethylbenzoyl chloride (Ⅲ) is obtained;

[0045] c): Chloride (Ⅲ) is pumped into the esterification kettle, and 80-120 parts of anhydrous methanol is added dropwise, and the esterification reaction is carried out ...

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Abstract

The invention discloses a methyl 3-(cyanomethyl)benzoate synthetic method. The method comprises the following steps: taking m-toluic acid as a starting material, adding sulphone chloride for an acylation reaction, and flowing into liquid chlorine for a chlorination reaction, adding non-aqueous methanol dropwise for an esterification reaction to prepare ester, adding toluene and sodium cyanide into a cyanation reaction still, raising the temperature for backflow, adding the ester dropwise, carrying out backflow for 2 hours to prepare the methyl 3-(cyanomethyl)benzoate, and after the reaction, adding water to extract the methyl 3-(cyanomethyl)benzoate. The methyl 3-(cyanomethyl)benzoate synthetic method is high in yield, avoids serious three-waste pollution, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a method for synthesizing methyl m-cyanomethylbenzoate. Background technique [0002] Ketoprofen is an excellent anti-inflammatory analgesic, and it is an economical and environmentally friendly route to synthesize ketoprofen with methyl m-cyanomethyl benzoate as a starting material, but traditional m-cyanomethyl benzoate The production process of methyl formate is complex, the cost is high, and the yield is low. For this reason, be badly in need of a kind of simple to operate on the market, with low cost and industrially produced m-cyanomethylbenzoic acid methyl ester synthetic method. The present inventor invented and created this application technology. Contents of the invention [0003] The object of the present invention is to provide a kind of synthetic method of methyl m-cyanomethylbenzoate with high yield, low cost, recycling, environmental prot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/41C07C253/14
Inventor 邵新华何正江徐亚华徐保华
Owner WUHAN INSTITUTE OF TECHNOLOGY
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