Synthetic method of methyl 2-fluoro-3-hydroxypropionate

A kind of technology of methyl hydroxypropionate and synthesis method, which is applied in the synthesis field of methyl 2-fluoro-3-chloropropionate, and can solve the problem that there is no good method for preparing methyl 2-fluoro-3-hydroxypropionate and other problems, to achieve the effect of low cost and high yield

Active Publication Date: 2018-04-03
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far there is no good method for preparing methyl 2-fluoro-3-hydroxypropionate

Method used

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  • Synthetic method of methyl 2-fluoro-3-hydroxypropionate
  • Synthetic method of methyl 2-fluoro-3-hydroxypropionate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment one: the synthesis of sodium enolate intermediate, methyl tert-butyl ether is used as solvent

[0019] Add methyl tert-butyl ether (1L), methyl fluoroacetate (460 g), and dimethyl oxalate (620 g) into a 5 L three-necked flask at 20 – 30 o C and stirred for 10 min. NaOMe / MeOH (27% by weight) solution (1050mL) was added dropwise, and the temperature was controlled at 20-30 o c. The color of the solution changed from colorless to yellow immediately. The dropwise addition is complete. Warm 20 – 30 o C reacted for 4 h. After filtration, the filter cake was slurried with methyl tert-butyl ether (500 mL), and suction filtered. Obtained 1 (840 g, 84 %) as a pale yellow solid.

[0020] Its reaction formula is:

[0021]

Embodiment 2

[0022] Embodiment two: the synthesis of sodium enolate intermediate, tetrahydrofuran is made solvent

[0023] Add tetrahydrofuran (1L), methyl fluoroacetate (460 g), and dimethyl oxalate (620 g) into a 5 L three-neck flask at 20 – 30 o C and stirred for 10 min. NaOMe / MeOH (27% by weight) solution (1050 mL) was added dropwise, and the temperature was controlled at 20-30 o c. The color of the solution changed from colorless to yellow immediately. The dropwise addition is complete. Warm 20 – 30 o C reacted for 4h. After filtration, the filter cake was slurried with tetrahydrofuran (500 mL), and suction filtered. Obtained 1 (870 g, 87 %) as a pale yellow solid.

Embodiment 3

[0024] Example Three: Methyl 2-fluoro-3-hydroxypropionate, N,N-dimethylformamide as solvent

[0025] Throw in 5.6L of N,N-dimethylformamide, and cool down to 0 in an ice-water bath o C, throw 700 g enol sodium salt and Na 2 CO 3 360 g of the mixture, at the same time start rapid (within 1 hour) dropwise addition of 37% HCHO aq 263 mL, the addition is complete, 0 - 10 o C, heat preservation reaction for 2 h, add 5L×3EA to extract three times, combine the organic phase, Na 2 SO 4 Dried, filtered, and the filtrate was evaporated to dryness to give 423.4 g, distilled, collected in 100 - 110 o Fraction between C. Yield 80%.

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Abstract

The invention relates to a synthesis method of 2-fluoro-methyl 3-hydroxypropionate. The method comprises the following two steps: step one: a sodium enol intermediate is generated under an alkaline condition with methyl fluoroacetate and dimethyl oxalate as raw materials; step two: the sodium enol intermediate has a reaction with a paraformaldehyde or formaldehyde aqueous solution in a solvent to generate 2-fluoro-methyl 3-hydroxypropionate. Cheap methyl fluoroacetate and dimethyl oxalate are taken as raw materials, and the solvent with a low cost is used, so that 2-fluoro-methyl 3-hydroxypropionate is low in cost, high in yield and suitable for large-scale production. In particular, generation of 2-fluoro-methyl 3-hydroxypropionate in a reaction of sodium enol and the paraformaldehyde or formaldehyde aqueous solution under an alkaline condition is a breakthrough in the field.

Description

technical field [0001] The invention relates to a method for synthesizing methyl 2-fluoro-3-chloropropionate. Background technique [0002] Methyl 2-fluoroacrylate and its derivatives are widely used in the pharmaceutical industry and material industry. However, methods for large-scale industrial production of such compounds have yet to be developed. One of the most striking is that the polymerized 2-fluoroacrylate can be used to make plastic optical fiber used in optical fiber communication. However, 2-fluoromethyl acrylate prepared in large quantities is easy to polymerize during long-term or high-temperature transportation (even if a polymerization inhibitor is added). And methyl 2-fluoro-3-hydroxypropionate is easy to synthesize methyl 2-fluoroacrylate. Methyl 2-fluoro-3-hydroxypropionate is very stable. But so far there is no good method for preparing methyl 2-fluoro-3-hydroxypropionate. Contents of the invention [0003] The technical problem to be solved by the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/343C07C67/00C07C69/738C07C69/675C07C69/653C07C67/327
CPCC07C67/00C07C67/327C07C67/343C07C69/738C07C69/675C07C69/653
Inventor 付伯桥覃彩芹吴波英
Owner HUBEI ENG UNIV
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