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Method for preparing beta-nitrostyrolene and derivatives thereof

A technology of nitrostyrene and derivatives, which is applied in the fields of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of small catalyst selection range, poor catalyst reuse, low catalyst activity, etc. The effect of good reusability, good industrialization prospect and high yield

Active Publication Date: 2014-01-08
湖州达立智能设备制造有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these reaction systems more or less need to use a large amount of toxic and harmful organic solvents, the catalyst activity is relatively low and the catalyst consumption is large, the substrate selection range of some catalysts is small, or the repeated use of some catalysts is poor.

Method used

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  • Method for preparing beta-nitrostyrolene and derivatives thereof
  • Method for preparing beta-nitrostyrolene and derivatives thereof
  • Method for preparing beta-nitrostyrolene and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Benzaldehyde (5mmol), nitromethane (5.5mmol), 1mmol ionic liquid [SFHEA] [HSO 4 ] were sequentially added to a 50mL single-necked bottle, stirred at 110°C for 2 hours, detected by TLC, the raw materials disappeared, the reaction solution was extracted with ethyl acetate, the organic phase was combined, the solvent was evaporated under reduced pressure, and the product was obtained by recrystallization from absolute ethanol, with a yield of 91 %, the content is 98%.

[0021] β-nitrostyrene:

[0022] 1 H NMR (400MHz, CDCl 3 ):δ7.86(d,1H,J=2.8Hz),7.46-6.98(m,6H);ESI-MS:m / z=150[M+H].

Embodiment 2

[0024] P-methoxybenzaldehyde (5mmol), nitromethane (5mmol), 1mmol ionic liquid [SFHEA][HSO 4 ] was added to a 50mL single-necked bottle, stirred at 110°C for 3 hours, detected by TLC, the raw materials disappeared, the reaction solution was extracted with ethyl acetate, the organic phase was combined, the solvent was evaporated under reduced pressure, and the product was obtained by recrystallization from absolute ethanol, with a yield of 95% , content 98%.

[0025] 4-Methyoxy-trans-β-nitrostyrene:

[0026] 1 H NMR (400MHz, CDCl 3 ):δ7.96(d,1H,J=2.8Hz),7.54-7.50(m,3H),6.95(d,2H,J=7.2Hz),3.87(s,3H);ESI-MS:m / z=180[M+H].

Embodiment 3

[0028] P-methoxybenzaldehyde (5mmol), nitromethane (10mmol), 5mmol ionic liquid [SFHEA][HSO 4 ] was added to a 50mL single-necked bottle, stirred at 130°C for 3 hours, detected by TLC, the raw materials disappeared, the reaction solution was extracted with ethyl acetate, the organic phase was combined, the solvent was evaporated under reduced pressure, and the product was obtained by recrystallization from absolute ethanol, with a yield of 96% , content 97%.

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Abstract

The invention discloses a method for preparing beta-nitrostyrolene and derivatives thereof. The method comprises the following steps: with novel multiple acidic ionic liquid prepared by utilizing ethanol amine as a raw material as a catalyst, carrying out a Henry condensation reaction on a nitroparaffin substance and an aromatic aldehyde substance under a normal pressure heating condition, and dewatering to obtain corresponding beta-nitrostyrolene and derivatives thereof, wherein the ionic liquid can be repeatedly used for multiple times. The method is simple to operate, high in yield, good in repeatability of a catalytic reaction system and free of any organic solvent, thereby having a good industrial prospect.

Description

Technical field: [0001] The invention relates to a method for preparing β-nitrostyrene and its derivatives through Henry condensation and dehydration using a novel ethanolamine-based multiple acidic functional ionic liquid as a catalyst under efficient, green and solvent-free conditions. Background technique: [0002] Nitroolefins are widely used in organic synthesis. It is mainly reflected in two aspects. One is that nitroalkenes become useful synthetic reagents due to the strong electron-withdrawing properties of nitro groups, such as being used in Diels-Alder reactions (J.Am.Chem.Soc.1986,108 ,3855.), Conjugate addition (Eur.J.Org.Chem.2002,1877.) and other reactions; Another application of nitroalkenes is to convert nitro functional groups into functional groups such as amino groups, becoming an important class of Organic Synthesis Diced (Chem.Soc.Rev.1991,20,95.). The synthesis strategy of nitroalkenes is generally obtained by Henry reaction and dehydration eliminatio...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C201/12C07C205/04C07C205/32C07C205/09C07C205/06C07C205/17C07D333/12
Inventor 应安国胡华南武承林王云龙
Owner 湖州达立智能设备制造有限公司
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