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Preparation method of methyl 3-methoxyacrylate

A technology of methyl methoxy acrylate and methyl dimethoxy propionate, which is applied in the field of preparation of chemical drug intermediates, can solve the problems of unsuitability for industrial production, excessive industrial waste, and high cost of raw materials, and achieve increased yield, The effect of protecting the environment, equipment and energy consumption is low

Active Publication Date: 2020-11-27
ANHUI JINGHE IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The total yield of this method can reach 72.6%, but it needs to use a large amount of bromine and sodium methoxide, the cost of raw materials is high, and there are many industrial wastes produced in the reaction process, which is not suitable for industrial production

Method used

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  • Preparation method of methyl 3-methoxyacrylate
  • Preparation method of methyl 3-methoxyacrylate
  • Preparation method of methyl 3-methoxyacrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Dissolve 20.00 g of diketene in 50 mL of methanol, add 50.49 g of anhydrous sodium carbonate at room temperature, slowly add 75.64 g of trimethyl orthoformate dropwise, and react at 25°C for 60 minutes. pressure (-0.095Mp, 65°C) to obtain a colorless oily liquid, which is the product methyl 3,3-dimethoxypropionate;

[0029] The reaction formula is as follows:

[0030]

[0031] (2) Add 28.19 g of methyl 3,3-dimethoxypropionate and 39.32 g of p-toluenesulfonic acid into a round bottom flask equipped with a thermometer and a condenser tube, and slowly raise the temperature to 160 o C, react for 7.5h, after the reaction is over, distill (70°C) to remove the by-product methanol, then distill under reduced pressure (-0.09Mpa), collect 165-172 o The fraction of C yielded 19.88 g of a colorless oily liquid product, methyl 3-methoxyacrylate (yield: 90%).

[0032] The reaction formula is as follows:

[0033]

Embodiment 2

[0035] (1) Dissolve 25.00 g of diketene in 50 mL of methanol, add 45.49 g of anhydrous sodium carbonate at room temperature, slowly add 70.64 g of trimethyl orthoformate dropwise, and react at 25°C for 60 minutes. pressure (-0.095Mp, 65°C) to obtain a colorless oily liquid, which is the product methyl 3,3-dimethoxypropionate;

[0036] (2) Add 25.19 g of methyl 3,3-dimethoxypropionate and 35.32 g of p-toluenesulfonic acid into a round bottom flask equipped with a thermometer and a condenser tube, and slowly raise the temperature to 160 o C, react for 7.5h, after the reaction is over, distill (65°C) to remove the by-product methanol, then distill under reduced pressure (-0.095Mp), collect 165-172 o C fraction, 20.1 g (yield: 87%) of colorless oily liquid product 3-methyl methoxyacrylate was obtained.

Embodiment 3

[0038] (1) Dissolve 18.00 g of diketene in 50 mL of methanol, add 49.49 g of anhydrous sodium carbonate at room temperature, slowly add 74.64 g of trimethyl orthoformate dropwise, and react at 25°C for 60 minutes. pressure (-0.095Mp, 65°C) to obtain a colorless oily liquid, which is the product methyl 3,3-dimethoxypropionate;

[0039](2) Add 28.59 g of methyl 3,3-dimethoxypropionate and 39.52 g of p-toluenesulfonic acid into a round-bottomed flask equipped with a thermometer and a condenser, and slowly raise the temperature to 160 o C, react for 7.5h, after the reaction is over, distill (65°C) to remove the by-product methanol, then distill under reduced pressure (-0.095Mp), collect 165-172 o The fraction of C yielded 19.78 g (yield: 91%) of a colorless oily liquid product, methyl 3-methoxyacrylate.

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Abstract

The invention relates to a synthetic method of methyl 3-methoxyacrylate. The method is characterized by comprising the following steps that: (1) methyl 3, 3-dimethoxypropionate is synthesized from ketene dimer and trimethyl orthoformate at 25-90 DEG C under the catalytic action of an alkaline substance by taking alcohols as a solvent, and the molar ratio of the ketene dimer to trimethyl orthoformate to the alkaline substance is controlled to be 1: (1.0-5.0): (0.5-5.0); and (2) after the reaction is finished, the methyl 3, 3-dimethoxypropionate is cracked under the action of a catalyst to generate 3-methoxy methyl acrylate, and controlling the molar ratio of the methyl 3, 3-dimethoxypropionate to the catalyst to be 1: (1.0-5.0) and the reaction temperature to be 100-200 DEG C. According tothe method, raw materials are cheap and easy to obtain; the synthesis method is simple to operate; the reaction conditions are mild; requirements on equipment are low; and requirements of industrial large-scale production are met.

Description

technical field [0001] The invention belongs to the technical field of preparation methods of chemical drug intermediates, in particular to a preparation method of methyl 3-methoxyacrylate. Background technique [0002] 3-Methoxymethyl acrylate is an important intermediate in organic synthesis, widely used in the fields of pesticides, medicine and polymer materials. It can be used for the synthesis of the insecticide flonicamid, the herbicide fenpyrazone, the fungicide silthiofacil, the medicine ceftibuten, and the modification of water-based polymers. It has a wide range of uses and a large demand. However, domestic industrial production is relatively small and depends on imports more. Therefore, it is of great significance to develop an efficient synthetic method to prepare methyl 3-methoxyacrylate. Literature survey found that the synthesis of methyl 3-methoxyacrylate generally has the following methods: [0003] Method 1: Wacker oxidation method. Using methyl acrylate...

Claims

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Application Information

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IPC IPC(8): C07C67/327C07C69/734
CPCC07C67/327C07C67/46C07C69/734C07C69/708C07C69/67Y02P20/584
Inventor 姜维强杨志健侯方方
Owner ANHUI JINGHE IND
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