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Synthetic method of m-fluorocinnamic acid

A technology of m-fluorocinnamic acid and a synthesis method, which is applied in the field of synthesis of m-fluorocinnamic acid, can solve the problems of low purity of crude product, large amount of solvent pyridine, long reaction time, etc. Synthesis reaction time and the effect of optimizing post-processing procedures

Active Publication Date: 2018-04-10
CHANGZHOU VOCATIONAL INST OF ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hong-Jia Zhang, Novartis ag, etc. used m-fluorobenzaldehyde and malonic acid as raw materials, pyridine as solvent, and piperidine as catalyst to prepare m-fluorocinnamic acid, but the reaction time was longer (24h), and the amount of solvent pyridine used Large, high cost, and after the reaction to distill off pyridine under reduced pressure, the operation is more troublesome, and the crude product has the disadvantages of low purity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 31g of m-fluorobenzaldehyde and 3.3g of pyridine into a four-necked flask, stir and heat to 90°C, stir and add 31.25g of malonic acid in 5 batches until it is completely dissolved, after adding malonic acid, raise the temperature to 110°C and stir Reflux for 90min. Add 75mL of 10% hydrochloric acid into the four-necked flask, and cool to room temperature. Suction filter, and wash the solid with hot water above 70°C until the pH of the washing liquid is neutral and the washing liquid is colorless. The solid was dried to obtain white flaky crystals with a yield of 79.5%.

Embodiment 2

[0016] Add 31g of m-fluorobenzaldehyde and 6.59g of pyridine into a four-neck flask, stir and heat to 90°C, stir and add 31.25g of malonic acid in 5 batches until it is completely dissolved, after adding malonic acid, raise the temperature to 110°C and stir Reflux for 120min. Add 75mL of 10% hydrochloric acid into the four-necked flask, and cool to room temperature. Suction filter, and wash the solid with hot water above 70°C until the pH of the washing liquid is neutral and the washing liquid is colorless. The solid was dried to obtain white flaky crystals with a yield of 85.5%.

Embodiment 3

[0018] Add 31g of m-fluorobenzaldehyde and 9.89g of pyridine into a four-neck flask, stir and heat to 90°C, stir and add 31.25g of malonic acid in 5 batches until it is completely dissolved, after adding malonic acid, raise the temperature to 110°C and stir Reflux for 150min. Add 85mL of 10% hydrochloric acid to the four-neck flask, and cool to room temperature. Suction filter, and wash the solid with hot water above 70°C until the pH of the washing liquid is neutral and the washing liquid is colorless. The solid was dried to obtain white flaky crystals with a yield of 74.7%.

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Abstract

The invention relates to a 3-fluorocinnamic acid synthesis method. The method includes steps: adding 3-fluorobenzaldehyde and pyridine into a reaction vessel, stirring and heating to 90-110 DEG C, adding malonic acid in batches while stirring until the malonic acid is dissolved completely, and performing stirring reflux for 1.5-2.5h at 90-110 DEG C; adding diluted hydrochloric acid into the reaction vessel, cooling to the room temperature, leaching to obtain solids, washing the solids with hot water until pH of washing liquor to be neutral and colorless, and drying to obtain a finished product. The 3-fluorocinnamic acid synthesis method has the advantages that consumption of solvents and catalysts is reduced, synthetic reaction time is shortened, aftertreatment procedures are optimized, and product purity is improved; purity of a crude product is 99.83%, and the purity reaches 99.95% after recrystallization.

Description

technical field [0001] The invention relates to a method for synthesizing m-fluorocinnamic acid. Background technique [0002] Meta-fluorocinnamic acid is an organic synthesis intermediate and chemical reagent, which is mostly used in organic synthesis, development of fine chemicals and drug research and development. [0003] The synthesis process of m-fluorocinnamic acid reported in foreign literature has disadvantages such as long reaction time, use of a large amount of solvent or catalyst, low product yield, and complicated operation. Burroughs Wellcome Co. uses m-fluorobenzaldehyde and malonic acid as raw materials (1:1.4), ethanol as solvent, pyridine and piperidine (2:1) as a mixed catalyst to obtain m-fluorocinnamic acid, and the reaction time of this method is Longer (8h), use raw material amount, solvent and catalyst all more, increased cost. Hong-Jia Zhang, Novartis ag, etc. used m-fluorobenzaldehyde and malonic acid as raw materials, pyridine as solvent, and pip...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/353C07C51/38C07C57/60
CPCC07C51/353C07C51/38C07C57/60
Inventor 李雪莲孙毓韬
Owner CHANGZHOU VOCATIONAL INST OF ENG
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