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Preparation method of 3, 4-dimethoxybenzonitrile

A technology of dimethoxybenzonitrile and dimethoxyphenylacetone is applied in the field of preparation of 3,4-dimethoxybenzonitrile, and can solve the problem of low yield, high reaction temperature and good yield and other problems, to achieve high yield, reduce pollution, and broaden the selection range.

Inactive Publication Date: 2020-06-19
HENAN AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention aims at the problems of high reaction temperature or low yield in the synthesis method of 3,4-dimethoxybenzonitrile in the prior art, and provides a preparation method of 3,4-dimethoxybenzonitrile , the method uses 3,4-dimethoxyphenylacetone as a raw material, and can achieve a good yield at a relatively mild reaction temperature

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

[0019] Add 0.5mmol 3,4-dimethoxyphenylacetone, 0.75mmol sodium nitrite, 0.025mmol iron complex A and 2mL dimethyl sulfoxide after dehydration and drying into the reaction tube, seal the reaction tube Reaction at 90°C for 20h (when the reaction tube was sealed, the air in the reaction tube was replaced by argon twice); after the reaction was finished, the gas chromatography internal standard method was used to carry out quantitative analysis, and the productive rate was 95%. The 3,4-dimethoxybenzonitrile product is separated and purified (mobile phase: a mixed solvent of sherwood oil and ethyl acetate with a volume ratio of 10:1), and the resulting product is detected by hydrogen spectrum and carbon spectrum, and the results are as follows: figure 1 and figure 2 shown, according to figure 1 shown 1 H-NMR and figure 2 shown 13 C-NMR confirms that the structure of product is as follows:

[0020]

Embodiment 2-3

[0022] Sodium nitrite in Example 1 is replaced with nitrogen dioxide and nitrogen monoxide in equimolar amounts respectively, and other conditions are the same as Example 1. The productive rate of 3,4-dimethoxybenzonitrile product is respectively 33% , 38%, it can be seen that when sodium nitrite is used as nitrogen oxide to react with the substrate, the yield is higher, while under the same reaction conditions, nitrogen dioxide and nitric oxide will cause the yield to decrease.

Embodiment 4-5

[0024] The complex of iron in embodiment 1 is replaced with iron trichloride, iron trifluoromethanesulfonate respectively of equimolar amount, other conditions are with embodiment 1. The production of 3,4-dimethoxybenzonitrile product The rates are 32% and 39% respectively. Due to the large difference in the spatial structure of these three catalysts, especially the spatial structure of the iron complex is quite different from that of ferric chloride and ferric trifluoromethanesulfonate, it shows a significantly higher catalytic activity than the latter two. .

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Abstract

The invention provides a preparation method of 3, 4-dimethoxybenzonitrile, which comprises the following steps of adding 3, 4-dimethoxyphenyl acetone and nitrogen oxide into an organic solvent, and carrying out catalytic reaction by an iron catalyst under the protection of inert gas to obtain the 3, 4-dimethoxybenzonitrile. According to the method, 3, 4-dimethoxyphenyl acetone is used as a raw material, so that high yield can be realized at a relatively mild reaction temperature.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 3,4-dimethoxybenzonitrile. Background technique [0002] 3,4-Dimethoxybenzonitrile has important uses in the chemical industry. It is a raw material for the production of various pesticides, and can also be used to prepare some herbicides, medicines and dyes. At present, there are many methods for synthesizing 3,4-dimethoxybenzonitrile, mainly as follows: (1) 3,4-dimethoxytoluene ammoxidation method (Catalysts Applied Catalyst A:General, 2001, the 208th volume, 21–34 pages); the method takes 3,4-dimethoxytoluene, ammonia and oxygen as raw materials, under the action of a catalyst, through the amination oxidation of methyl in 3,4-dimethoxytoluene, To produce 3,4-dimethoxybenzonitrile products. (2) Aldoxime dehydration method (Tetrahedron Letters, 2016, volume 57, pages 5700–5702); this method uses 3,4-dimethoxybenzaldehyde, 3,4-dimet...

Claims

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Application Information

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IPC IPC(8): C07C253/02C07C255/54
CPCC07C253/02C07C255/54
Inventor 任运来田欣哲申振鹏赵哲刘文波
Owner HENAN AGRICULTURAL UNIVERSITY
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