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Preparation method of 3, 4-dimethoxybenzonitrile

A technology of dimethoxybenzonitrile and dimethoxybenzene, which is applied in the field of preparation of chemical raw materials, can solve the problems of high-energy chemical bond carbon-carbon bond breakage, difficult reaction, etc., achieves low toxicity, simple steps, and reduced process cost Effect

Active Publication Date: 2020-01-10
河南睿嵩检测技术有限公司
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  • Application Information

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Problems solved by technology

However, in the conversion reaction process of 3,4-dimethoxyphenylacetic acid to 3,4-dimethoxybenzonitrile, it involves the breaking of high-energy chemical bond carbon-carbon bonds, and there is a problem that the reaction is difficult to proceed smoothly.

Method used

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  • Preparation method of 3, 4-dimethoxybenzonitrile
  • Preparation method of 3, 4-dimethoxybenzonitrile
  • Preparation method of 3, 4-dimethoxybenzonitrile

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Take magneton, 2 mL dimethyl sulfoxide, 0.5 mmol 3,4-dimethoxyphenylacetic acid, 3 mmol sodium nitrite and 0.5 mmol ferric chloride and add them to the glass pressure-resistant reaction tube in turn, after that, the reaction The tube was sealed and placed in a heating tank at a temperature of 50° C., and heated for 10 h under magnetic stirring. After the reaction, the reaction system was cooled to room temperature.

[0027] Afterwards, the internal standard quantitative analysis of the above reaction product was carried out by gas chromatography, and the yield of 3,4-dimethoxybenzonitrile product was measured to be 82%.

[0028] Then the above experimental steps were repeated, and after the reaction system was cooled to room temperature, the product was separated and purified by column chromatography to obtain the purified 3,4-dimethoxybenzonitrile finished product. use 1 H-NMR, 13 C-NMR confirms the structure of the product in the appendix figure 1 And attached f...

Embodiment 2-7

[0030] Change the consumption of sodium nitrite into 1mmol, 1.5mmol, 2mmol, 2.5mmol, 3.5mmol, 4mmol respectively in the embodiment 1, other conditions are constant, draw the productive rate of product (gas phase internal standard) to be respectively 20%, 51%. %, 70%, 75%, 90%, 89%.

Embodiment 8-11

[0032] Change the consumption of ferric chloride in embodiment 1 into 0.25mmol, 1mmol, 1.5mmol, 2mmol respectively, other conditions are constant, draw the productive rate of product (gas phase internal standard) to be 43%, 82%, 75% respectively , 63%, 47%.

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Abstract

A preparation method of 3,4-dimethoxybenzonitrile is characterized in that 3,4-dimethoxyphenylacetic acid and sodium nitrite are used as raw materials, and ferric trichloride is used as a catalyst. The preparation method which is different from previous synthesis methods has the following characteristics: the used raw materials are cheap and easily available phenylacetic acid compounds, and the sodium nitrite is used as a nitrogen source, so the toxicity of the raw materials is low, and the price is low. The problem of high comprehensive cost of materials such as reaction reagents used in theexisting method is solved. The preparation method of the 3,4-dimethoxybenzonitrile has the advantages of low toxicity, simple process, mild conditions and high finished product yield.

Description

technical field [0001] The invention relates to the technical field of preparation of chemical raw materials, in particular to a preparation method of 3,4-dimethoxybenzonitrile. Background technique [0002] 3,4-Dimethoxybenzonitrile is a widely used chemical intermediate, which can be used in the synthesis of medicines, herbicides and dyes (Chem. Commun., 2017, 53, 1048-1051). At present, the synthesis methods of 3,4-dimethoxybenzonitrile in the prior art mainly include: (1) amide dehydration method. The basic raw material of this method is 3,4-dimethoxybenzamide (Indian J.Chem. Sect. B, 2003, 42, 3148-3151), through the action of phosphorus pentachloride and other dehydrating agents, to obtain 3, 4-dimethoxybenzonitrile product. (2) Aldoxime dehydration method (Synth. Commun., 2004, 34, 2025-2030). In this method, 3,4-dimethoxybenzaldehyde is generally used as a raw material, and aldoxime is obtained through the reaction of aldehyde and hydroxylamine, and the aldoxime i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/02C07C255/54C01B21/24
CPCC07C253/02C01B21/24C07C255/54
Inventor 代红兵李晴媛马芳吴青刘志飞张轲周韶波刘晨嵩
Owner 河南睿嵩检测技术有限公司
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