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Preparation method of methyl 3-methoxyacrylate

A technology of methyl methoxyacrylate and methyl oxypropionate is applied in the field of preparation of methyl 3-methoxyacrylate, can solve problems such as low boiling point, strong volatility, etc. Ease of transportation and storage

Inactive Publication Date: 2014-09-24
HUNAN HAILI CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The raw material 3-methoxy-3-ethoxypropionate methyl ester used in the method is synthesized by vinyl ether and trichloroacetyl chloride, but vinyl ether has low boiling point (33.0° C.) and strong volatility. Transport and storage require specialized equipment

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
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Effect test

Embodiment 1

[0022] Add 38g (200mmol) methyl 3-methoxy-3-butoxypropionate, 190g methanol, and 1.9g potassium hydrogensulfate to a 500mL three-necked flask equipped with mechanical stirring, a thermometer and a reflux device, and heat to reflux after adding After 24 hours, the reflux device was changed to a vacuum distillation device, and the solvent was removed under reduced pressure. Under the protection of nitrogen, the residue was heated to 160 ° C for 5 hours for cracking reaction, and then distilled under reduced pressure to obtain 18.2 g of 3-methoxymethyl acrylate with a purity of 96%. The yield of methyl ester was 75.3%.

Embodiment 2

[0024] Add 38g (200mmol) methyl 3-methoxy-3-butoxypropionate, 190g methanol, and 0.38g potassium hydrogensulfate to a 500mL three-neck flask equipped with mechanical stirring, a thermometer and a reflux device, and react at 40°C after adding After 15 hours, the reflux device was changed to a vacuum distillation device, and the solvent was removed under reduced pressure. Under the protection of nitrogen, the residue was heated to 120 ° C for 5 hours for cracking reaction, and then distilled under reduced pressure to obtain 16.6 g of 3-methoxymethyl acrylate with a purity of 95%, which was converted to 3-methoxy-3-butoxypropionic acid The yield in terms of methyl ester was 68.0%.

Embodiment 3

[0026] Add 38g (200mmol) methyl 3-methoxy-3-butoxypropionate, 570g methanol, and 1.14g sodium bisulfate to a 1000mL three-neck flask equipped with mechanical stirring, a thermometer and a reflux device, and react at 55°C after adding After 10 hours, the reflux device was changed to a vacuum distillation device, and the solvent was removed under reduced pressure. Under the protection of nitrogen, the residue was heated to 180° C. for 5 hours, and then distilled under reduced pressure to obtain 18.2 g of methyl 3-methoxyacrylate with a purity of 97%. The yield of methyl ester was 76.1%.

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Abstract

The invention discloses a preparation method of methyl 3-methoxyacrylate. Methyl 3-methoxy-3-R-oxypropionate and methanol used as raw materials react to prepare the methyl 3-methoxyacrylate by a one-pot process under the action of a catalyst potassium hydrogen sulfate, sodium bisulfate or p-toluenesulfonic acid. The chemical equation is disclosed in the specification, wherein R represents propyl or butyl group. The raw material methyl 3-methoxy-3-R-oxypropionate can be conveniently prepared from vinyl R ether and trichloro-acetic chloride; and the vinyl R ether has higher boiling point, and thus, is convenient for transportation and storage. The methyl 3-methoxy-3-R-oxypropionate and methanol are synthesized into the target product by the one-pot process under the action of the catalyst; and thus, the method is simple and easy to operate, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of methyl 3-methoxyacrylate. Background technique [0002] Methyl 3-methoxyacrylate is an important pharmaceutical and pesticide intermediate, which is widely used in the fields of medicine and polymer materials, and can be used to synthesize the pharmaceutical product ceftibuten; it can also be used as the insecticide sulfoxetin Intermediates of amides. According to literature reports, there are mainly the following synthetic methods at home and abroad. [0003] One, the document Journal of Organic Chemistry, 2010,75(22), 7809-7821 reports that methyl propiolate is used as a raw material, and methanol is added to obtain methyl 3-methoxyacrylate under the action of a catalyst. rate of 71%. [0004] [0005] The raw material methyl propiolate used in the method is expensive, resulting in higher costs. [0006] 2. Document WO2009056293 reports that methyl 3,3-dimethoxypropionate was used as a raw mater...

Claims

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Application Information

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IPC IPC(8): C07C67/327C07C69/734
CPCC07C67/327C07C67/31
Inventor 罗亮明胡志彬黄超群杜升华熊莉莉
Owner HUNAN HAILI CHEM IND
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