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Synthesis method of methyl-alpha-fluoroacrylate and analogues thereof

A technology for the synthesis of methyl fluoroacrylate, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, can solve problems such as low yield, insufficient product purity, and unsuitability for industrial production, and achieve The effect of low preparation cost and high yield

Inactive Publication Date: 2011-10-12
RADIANT PHARMA & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the sodium hydrogen used in the reaction process, ether, etc. are not suitable for industrial production, and the yield of 30% is too low, and at the same time, the purity of the product is not enough

Method used

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  • Synthesis method of methyl-alpha-fluoroacrylate and analogues thereof
  • Synthesis method of methyl-alpha-fluoroacrylate and analogues thereof
  • Synthesis method of methyl-alpha-fluoroacrylate and analogues thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Synthesis of α-methyl fluoroacrylate - no separation of intermediates

[0031] Methyl fluoroacetate (20 g, 0.217 mol) and dimethyl oxalate (25.6 g, 0.217 mol) were added to 100 ml of diphenyl ether, sodium methoxide solid (11.7 g, 0.217 mol) and hydroquinone (0.2 g), heated to 30-40°C and stirred for 5 hours, added paraformaldehyde (6.5g, 0.217mol), kept the temperature at 30-40°C and stirred for 5 hours, directly steamed the product under reduced pressure with a water pump, washed with 5 ml of saturated brine for 2 Once, dried over sodium sulfate to obtain 6.77 grams of product with a yield of 30% and a gas phase purity of 95%. Its reaction formula is:

[0032]

Embodiment 2

[0033] Example 2: Synthesis of α-methyl fluoroacrylate intermediate enol sodium salt, tert-butyl methyl ether as solvent

[0034] Add methyl fluoroacetate (92g, 1mol) and dimethyl oxalate (118g, 1mol) into 500ml of tert-butyl methyl ether, add solid sodium methoxide (54g, 1mol), heat to 30-40°C and stir for 5 hours, Cool to 20° C., filter, wash with 100 ml of tert-butyl methyl ether, and vacuum-dry at 50° C. for 5 hours to obtain 198 g of white or light yellow solid powder with a yield of 99%.

Embodiment 3

[0035] Example 3: Synthesis of α-methyl fluoroacrylate intermediate enol sodium salt, using ethylene glycol dimethyl ether as a solvent

[0036] Add methyl fluoroacetate (92g, 1mol) and dimethyl oxalate (118g, 1mol) to 500ml of ethylene glycol dimethyl ether, add solid sodium methoxide (54g, 1mol), heat to 30-40°C and stir for 5 hours, cooled to ℃, filtered, washed with 100 ml of ethylene glycol dimethyl ether, and vacuum-dried at 50°C for 5 hours to obtain 190 g of white or light yellow solid powder with a yield of 95%.

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Abstract

The invention relates to a synthesis method of methyl-alpha-fluoroacrylate and analogues thereof. The method comprises the following steps: step 1, based on methyl fluoroacrylate and dimethyl oxalate serving as raw materials, dissolving the raw materials in a solvent, and adding base for carrying out condensation reaction so as to generate sodium enolate or potassium enolate intermediate; and step 2, reacting sodium enolate or potassium enolate intermediate with paraformaldehyde or trioxane in the solvent so as to generate methyl-alpha-fluoroacrylate. According to the invention, cheap methyl fluoroacrylate and dimethyl oxalate are used as the raw materials, and the low-cost solvent and other reactants are selected, thus the method has the advantages of low preparation cost and high yield and can be suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing α-methyl fluoroacrylate and its analogues. Background technique [0002] In the past decade, methyl α-fluoroacrylate and its analogues have been widely used in the pharmaceutical industry and material industry, however, the large-scale industrial production methods of these compounds are still to be developed. Acrylate-based polymers are of great significance in modern material chemistry. For example, in the information industry, optical fiber communication has become an important part of the information highway. Optical fibers are divided into two types: quartz optical fibers and plastic optical fibers. Plastic optical fibers (POF, Plastic Optical Fiber) is an optical fiber made of a light-transmitting polymer. Because the mature and simple drawing process of the polymer can be used, the cost is relatively low, and it is relatively soft, strong, and has a large diameter (about 1mm ), the connection l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/653C07C67/475C07C67/54
Inventor 张飞罗治斌张昌朋王森胡颖健
Owner RADIANT PHARMA & TECH
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