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Preparing method of 3-fluoroacetone acid

A technology of fluoropyruvate and ethyl acetate, which is applied in the field of preparation of 3-fluoropyruvate, can solve the problems of low yield, high production cost, and difficult synthesis, and achieve simple reaction process conditions and low production cost. Low, environmentally friendly effect

Active Publication Date: 2017-08-18
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are very few reports on the synthesis of 3-fluoropyruvate. In the report, the synthesis of 3-fluoropyruvate as the target product has a complex structure of starting materials, difficult synthesis, long reaction steps, and low yield. High cost, unable to realize industrial production

Method used

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  • Preparing method of 3-fluoroacetone acid
  • Preparing method of 3-fluoroacetone acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 600ml tetrahydrofuran, NaH solid (24.0g, 1.00mol) and diethyl oxalate (140.0g, 0.95mol) into a 1L four-necked round bottom flask equipped with mechanical stirring, slowly Ethyl fluoroacetate (100.0 g, 0.94 mol) was slowly added dropwise, and the reaction was carried out at 70° C. for 6 h after the addition was completed. Add 400ml of toluene, 500.0g of ice, and 88ml of concentrated hydrochloric acid (mass concentration 36-38%) into a 2L beaker, cool down to 0°C, and slowly add the reaction solution dropwise to the 2L beaker to quench excess NaH. Separation, the aqueous layer was extracted with toluene (100ml x 3), the organic phases were combined, after reclaiming the toluene solvent, rectification, and the gas phase temperature of 100-101 ° C was collected to obtain diethyl 2-fluoro-3-oxosuccinate ( 168.9g, 0.82mol), the gas chromatography detection purity is 99.9%, and the yield is 86.9%.

[0026] Gas chromatography testing conditions: Chromatographic column: cap...

Embodiment 2

[0030] Add 1000ml tetrahydrofuran, sodium methoxide solid (80.0g, 2.00mol), diethyl oxalate (280.0g, 1.9mol) in a 2L four-necked round bottom flask equipped with mechanical stirring, and use a constant pressure dropping funnel at room temperature Ethyl fluoroacetate (200.0 g, 1.88 mol) was slowly added dropwise, and the reaction was carried out at 65° C. for 6 h after the addition was complete. Add 400ml of toluene, 1000.0g of ice, and 180ml of concentrated hydrochloric acid (mass concentration 36-38%) into a 5L beaker. Excess sodium hydride. Separation, the aqueous layer was extracted with toluene (100ml x 3), the organic phases were combined, after reclaiming the toluene solvent, rectification, and the gas phase temperature of 100-101 ° C was collected to obtain diethyl 2-fluoro-3-oxosuccinate ( 323.4g (1.57mol), gas chromatography detection purity: 99.9%, yield: 83.5%.

[0031] Add diethyl 2-fluoro-3-oxosuccinate (323.4 g, 1.57 mol) and 200 ml of concentrated hydrochloric...

Embodiment 3

[0033] Add 1000ml tetrahydrofuran, sodium ethoxide solid (136.0g, 2.00mol) and diethyl oxalate (328.0g, 2.28mol) in a 2L four-neck round-bottomed flask equipped with mechanical stirring. Ethyl fluoroacetate (200.0 g, 1.88 mol) was slowly added dropwise, and the reaction was carried out at 60° C. for 6 h after the addition was completed. Add 400ml of toluene, 1000.0g of ice, and 180ml of concentrated hydrochloric acid (mass concentration 36-38%) into a 5L beaker. Excess sodium ethoxide. Separation, the aqueous layer was extracted with toluene (100ml x 3), the organic phases were combined, after reclaiming the toluene solvent, rectification, and the gas phase temperature of 100-101 ° C was collected to obtain diethyl 2-fluoro-3-oxosuccinate ( 327.6g (1.59mol), the gas chromatography detection purity is 99.9%, and the yield is 84.6%.

[0034] Add diethyl 2-fluoro-3-oxosuccinate (327.6g, 1.59mol) into a 1L four-neck flask equipped with mechanical stirring, 200ml of concentrated ...

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Abstract

The invention relates to a preparing method of 3-fluoroacetone acid. Diethyl oxalate and fluoro ethyl acetate are adopted as raw materials, NaH is adopted as a strong base catalyst to conduct an ester condensation reaction to obtain 2-fluo-3-oxo diethyl succinate, wherein the yield rate is 84.6%, and the gas phase chromatographic detection purity is 99.9%. 2-fluo-3-oxo diethyl succinate is put into an acid solution, and then through hydrolysis and decarboxylation reactions, and then through distillation and water removal, a coarse product is obtained, and finally through a sublimation method, 3-fluoroacetone acid is obtained, the yield rate is 85.4%, the liquid phase chromatographic detection purity is 99.9%, and the total yield through the two steps is 72%. The reaction technology is simple in condition, reactions are all conventional reactions under the normal pressure, the operation is simple and convenient, the raw materials are easy to obtain, and the product cost is low.

Description

[0001] (1) Technical field [0002] The invention relates to a preparation method of 3-fluoropyruvate. [0003] (2) Background technology [0004] 3-Fluoropyruvate is a white crystal with a structure similar to that of pyruvic acid. Since the volume of fluorine atoms is equivalent to that of hydrogen atoms, it will be mistaken for recognition and absorption of pyruvic acid in biological cells. At the same time, due to the chemical characteristics of fluorine atoms , which endows 3-fluoropyruvate with special toxicological activity on organisms, so it has a wide range of applications in pesticides and medicine. At present, there are very few reports on the synthesis of 3-fluoropyruvate. In the report, the synthesis of 3-fluoropyruvate as the target product has a complex structure of starting materials, difficult synthesis, long reaction steps, and low yield. The cost is high, and industrialized production cannot be realized. [0005] (3) Contents of the invention [0006] The...

Claims

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Application Information

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IPC IPC(8): C07C59/21C07C51/38C07C51/43C07C67/343C07C69/716
CPCC07C51/38C07C51/43C07C67/343C07C69/716C07C59/21
Inventor 丁成荣潘亚运张国富吕井辉
Owner ZHEJIANG UNIV OF TECH
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