Preparation method of cinnamic acid or derivatives thereof

A technology of derivatives and cinnamic acid, which is applied in the field of preparation of cinnamic acid or its derivatives, can solve problems such as adverse effects on the nervous system and respiratory tract, difficulties in industrial scale-up production, and environmental pollution from emissions, so as to avoid the use of toxic catalysts and overcome It is difficult to recover raw materials and avoid the effect of high temperature reaction

Inactive Publication Date: 2014-08-27
褚朝森
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The Knoevenagel method needs to use pyridine, piperidine, etc. as catalysts, and its strong irritation will have adverse effects on the nervous system and respiratory tract, and it is difficult to recover benzaldehyde, pyridine, and piperidine , the discharge will bring serious environmental pollution, and there are certain difficulties in industrial scale-up production

Method used

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  • Preparation method of cinnamic acid or derivatives thereof
  • Preparation method of cinnamic acid or derivatives thereof
  • Preparation method of cinnamic acid or derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1, a kind of preparation method of cinnamic acid or derivative thereof, its steps are as follows:

[0036] (1) Esterification reaction: Add triethyl phosphonoacetate in dichloromethane solution into the reaction vessel, slowly add sodium hydride under stirring at -5°C, raise the temperature to 20°C, quickly add the raw material aldehyde, and react at room temperature for 2~ After 6 hours, add a saturated aqueous solution of ammonium chloride and stir, the organic phase is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution, the solvent is removed under reduced pressure, and purified by column chromatography to obtain a light yellow oil;

[0037] In the esterification reaction, the ratio of the amount of raw materials is, aldehyde: triethyl phosphonoacetate: sodium hydride=1:1.2:2.5;

[0038] Described aldehyde is selected from benzaldehyde, p-methoxybenzaldehyde, p-chlorobenzaldehyde, p-fluorobenzaldehyde, 2-t...

Embodiment 2

[0041] Embodiment 2, a kind of preparation method of cinnamic acid or derivative thereof, its steps are as follows:

[0042] (1) Esterification reaction: Add triethyl phosphonoacetate in dichloromethane solution into the reaction vessel, slowly add sodium hydride under stirring at 5°C, raise the temperature to 30°C, quickly add raw material aldehyde, and react at room temperature for 2-6 hour, add a saturated aqueous solution of ammonium chloride and stir, the organic phase is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution successively, the solvent is removed under reduced pressure, and purified by column chromatography to obtain a light yellow oil;

[0043] In the esterification reaction, the ratio of the amount of raw materials is, aldehyde: triethyl phosphonoacetate: sodium hydride=1: 1.8: 3.5;

[0044] Described aldehyde is selected from benzaldehyde, p-methoxybenzaldehyde, p-chlorobenzaldehyde, p-fluorobenzaldehyde, 2-thiophene fo...

Embodiment 3

[0047] Embodiment 3, a kind of preparation method of cinnamic acid or derivative thereof, its steps are as follows:

[0048](1) Esterification reaction: Add triethyl phosphonoacetate in dichloromethane solution into the reaction vessel, slowly add sodium hydride under stirring at 0°C, raise the temperature to room temperature, quickly add the raw material aldehyde, and react at room temperature for 2 to 6 hours , adding a saturated aqueous solution of ammonium chloride and stirring, the organic phase was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution successively, the solvent was removed under reduced pressure, and purified by column chromatography to obtain a light yellow oil;

[0049] In the esterification reaction, the ratio of the amount of raw materials is, aldehyde: triethyl phosphonoacetate: sodium hydride=1:1.5:3;

[0050] Described aldehyde is selected from benzaldehyde, p-methoxybenzaldehyde, p-chlorobenzaldehyde, p-fluoroben...

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Abstract

The invention discloses a preparation method of cinnamic acid or derivatives thereof. The method comprises the following steps: adding a dichloromethane solution of triethyl phosphonoacetate, sodium chloride and raw material aldehyde into a reaction container, performing room-temperature reaction, adding a saturated water solution of ammonium chloride, stirring, performing organic phase washing, performing reduced pressure treatment to remove a solvent, and performing column chromatography purification to obtain a light yellow oily product; adding a mixed solution of dichloromethane and methanol into a reaction product, stirring, dropwise adding a methanol solution of sodium hydroxide to generate a large quantity of turbid materials, performing reduced pressure distillation on a reaction solution until the reaction solution is dry, removing impurities, extracting, combining organic phases, drying, performing reduced pressure treatment to remove the solvent, and drying in vacuum to obtain a white or light yellow product. According to the method, triethyl phosphonoacetate is adopted as an activating reagent for condensation esterification with aldehyde and then the product is conveniently prepared through alkaline hydrolysis; the reaction can be carried out at room temperature, and the shortcomings of low yield, high reaction temperature, high toxicity and serious pollution in a conventional process are overcome.

Description

technical field [0001] The invention relates to a method for preparing chemical raw materials, in particular to a method for preparing cinnamic acid or derivatives thereof. Background technique [0002] Cinnamic acid, also known as cinnamic acid, cinnamic acid, and 1,3-phenylacrylic acid, is one of the important industrial intermediates of organic synthesis. In addition to being used as a spice, it is widely used in medicine, plastics, food additives, and the preparation of photosensitive resins. In the pharmaceutical industry, it is used for the synthesis of important drugs for the treatment of coronary heart disease, such as lactodin, xintongping and Xinkean, and the synthesis of chlorphenamine and cinnamon phenylpiperazine; it can be used to manufacture local anesthetics, fungicides, hemostatic drugs, etc. ; It is also an effective inhibitor of human lung adenocarcinoma cells, and has great application value in anticancer. [0003] In the current technology, the main sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C27/02C07C57/44C07C59/64C07C57/60C07D333/24
CPCC07C51/09C07C67/44C07D333/24C07C57/44C07C59/64C07C57/60C07C69/618C07C69/734C07C69/65
Inventor 王晓丽褚朝森王政
Owner 褚朝森
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