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Preparation method of beta-trans-nitroolefin

A nitroalkene and trans technology, which is applied in the field of preparation of beta-trans nitroalkene, and achieves the effects of wide application range of substrates, good tolerance and high product yield

Active Publication Date: 2020-06-02
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No visible light catalyzed reaction between alkenes and copper nitrate to prepare β-trans nitroalkenes has been found

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 A method for preparing β-trans-nitroolefins, the method refers to: sequentially add styrene, nickel nitrate, and acetonitrile into a reaction vessel and mix evenly, and keep the temperature at 30°C under the irradiation of a 36 W compact fluorescent lamp After 18 hours of reaction, the reaction solution was obtained.

[0015] Among them: the molar ratio of styrene and nickel nitrate is 1:2.

[0016] The whole reaction process was tracked by thin layer chromatography, that is, samples were taken every 1 hour, and the reaction liquid and raw material liquid styrene were respectively dripped on the silica gel plate with a capillary tube, and then the silica gel plate was placed in a volume ratio (mL / mL) In the display bottle of 20:1 petroleum ether / ethyl acetate mixture. After the plate movement is completed, place the silica gel plate under a UV lamp or in an iodine bottle for observation. The reaction is complete if there is no point flush with the starting m...

Embodiment 2

[0018] Example 2 A method for preparing β-trans-nitroolefins, the method refers to: sequentially add styrene, silver nitrate, and 1,4-dioxane into a reaction vessel and mix them uniformly, at 20°C at 20 Under constant temperature reaction for 18 h under the irradiation of a compact fluorescent lamp, a reaction solution was obtained.

[0019] Among them: the molar ratio of styrene and silver nitrate is 1:2.

[0020] The whole reaction process was tracked according to the thin-layer chromatography method described in Example 1 to obtain the reaction solution; the reaction solution was successively concentrated and separated by column chromatography according to the method described in Example 1 to obtain (E)- β - Nitrostyrene, yield 55%.

Embodiment 3

[0021] Example 3 A preparation method of β-trans-nitroolefins, the method refers to: sequentially add 4-tert-butylstyrene, sodium nitrite, tetrahydrofuran into the reaction vessel and mix evenly, at 60 ° C under 36 W Under the irradiation of a compact fluorescent lamp, react at a constant temperature for 18 hours to obtain a reaction solution.

[0022] Among them: the molar ratio of 4-tert-butylstyrene to sodium nitrite is 1:2.

[0023] The whole reaction process was tracked according to the thin-layer chromatography method described in Example 1 to obtain the reaction solution; the reaction solution was concentrated and separated by column chromatography according to the method described in Example 1 to obtain (E)-4-tert-butyl - β - Nitrostyrene, yield 42%.

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PUM

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Abstract

The invention relates to a preparation method of beta-trans-nitroolefin. The method comprises: sequentially adding an olefin compound, a nitration reagent and a solvent into a reaction container, mixing the substances uniformly, and carrying out constant temperature reaction for 18h under an illumination condition to obtain a reaction solution; and sequentially carrying out drying, concentration and column chromatography treatment on the reaction solution to obtain the beta-trans-nitroolefin compound. The method is simple and practicable, low in cost and high in product yield, can realize large-scale production, and has good industrial application prospects in the aspects of functional organic material, bioactive compound and drug synthesis.

Description

technical field [0001] The invention relates to the field of organic synthesis chemistry, in particular to a preparation method of β-trans nitroolefins. Background technique [0002] β-trans-nitroolefin compounds are the basic raw materials for the synthesis of most dyes and polymers, and have very important applications in the fine chemical industry and the synthesis of pharmaceuticals and agricultural chemicals. In particular, in recent years, β-trans-nitroalkene compounds, as important intermediates in natural medicine and chemical industry, have attracted more and more attention of scientists. Therefore, many researchers have done a lot of work on the direct nitration of alkenes and made great achievements. [0003] At present, the published synthesis methods of nitroalkene compounds are as follows: (1) Nitromethane was used as a nitrating reagent in the early stage to directly participate in the reaction to synthesize nitroalkenes. For example, the Wadgaonker research...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/08C07C205/04
CPCC07C201/08C07C205/04Y02B20/00
Inventor 杜正银李怀贵张文莹李梦婷
Owner NORTHWEST NORMAL UNIVERSITY
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