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Method for catalyzing Knoevenagel condensation reaction by using function ion liquid

A technology of functional ionic liquids and condensation reactions, applied in chemical instruments and methods, preparation of organic compounds, catalysts for physical/chemical processes, etc., can solve problems such as the use of toxic and harmful solvents, cumbersome post-reaction treatment, long reaction time, etc., to achieve Inexpensive, reusable, adjustable molecular structure

Inactive Publication Date: 2013-10-16
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above methods have achieved some results, there are more or less problems in these methods, such as: long reaction time, low yield, cumbersome post-reaction treatment and the use of some toxic and harmful solvents

Method used

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  • Method for catalyzing Knoevenagel condensation reaction by using function ion liquid
  • Method for catalyzing Knoevenagel condensation reaction by using function ion liquid
  • Method for catalyzing Knoevenagel condensation reaction by using function ion liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add benzaldehyde (5mmol), malononitrile (6mmol), 4mL water, and 0.25mmol ionic liquid [Ch][OMe] into a 50mL single-necked flask in sequence, stir at room temperature for 1 minute, TLC detection, the raw materials disappeared, filtered, and vacuum-dried Cake obtains product, yield 98%, content 99%.

[0025] 2-(Phenylmethylene)-malononitrile:white solid;mp79-80℃; 1 H NMR (400 MHz, CDCl 3 )(ppm):7.91(d,2H,J=7.6Hz,ArH),7.79(s,1H,C=CH),7.64(t,1H,J=7.6Hz,ArH),7.27(t,2H, J=7.6Hz,ArH),7.27(t,2H,J=7.6Hz,ArH); 13 CNMR (100MHz, CDCl 3 )(ppm): 160.0, 134.6, 130.9, 130.7, 129.6, 113.7, 112.5, 82.7.

Embodiment 2

[0027] Add p-tolualdehyde (5mmol), malononitrile (6mmol), 4mL water, and 0.25mmol ionic liquid [Ch][OMe] into a 50mL single-necked bottle in turn, stir at room temperature for 1 minute, TLC detection, raw materials disappear, filter, Vacuum drying the filter cake to obtain the product with a yield of 99% and a content of 98%.

[0028] 2-(4-Methylphenylmethylene)malononitrile:white solid;mp134-135℃; 1 HNMR (400MHz, CDCl 3 )(ppm):7.82(d,2H,J=8Hz,ArH),7.73(s,1H,C=CH),7.34(d,2H,J=8Hz,ArH),2.46(s,3H,CH 3 ); 13 C NMR (100MHz, CDCl 3 )(ppm): 159.8, 146.4, 130.9, 130.3, 128.4, 114.0, 112.8, 81.1, 22.0.

Embodiment 3

[0030] Add p-nitrobenzaldehyde (5mmol), malononitrile (7.5mmol), 4mL water, and 5mmol ionic liquid [Ch][OMe] into a 50mL single-necked bottle in sequence, stir at room temperature for 0.5 minutes, TLC detection, raw materials disappear, filter , Vacuum drying the filter cake to obtain the product with a yield of 87% and a content of 97%.

[0031] 2-(4-Nitrophenylmethylene)malononitrile:yellow solid;mp136-138℃; 1 HNMR (400MHz, CDCl 3 )(ppm):8.46(s,1H,C=CH),8.32-8.29(d,1H,m,ArH),7.91-7.88(m,1H,ArH),7.84-7.80(m,2H,ArH) ; 13 C NMR (100MHz, CDCl 3 )(ppm): 158.9, 146.7, 134.9, 133.4, 130.4, 126.6, 125.8, 112.2, 110.9, 88.4.

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Abstract

The present invention discloses a method for catalyzing a Knoevenagel condensation reaction by using a function ion liquid. The method comprises that: a choline chloride function ion liquid is adopted as a catalyst, and aromatic aldehyde and an active methylene compound are subjected to a catalysis condensation reaction at a room temperature under a normal pressure to obtain a condensation product. The method has the following characteristics that: operations are simple, a yield is high, the catalysis reaction system has good reusability, reaction conditions are mild, and good industrialization prospects are provided.

Description

technical field [0001] The invention relates to a high-efficiency, green Knoevenagel condensation method of aromatic aldehydes and active methylene compounds using water as a reaction medium and choline chloride functional ionic liquid as a catalyst. Background technique [0002] The Knoevenagel condensation reaction is the condensation and dehydration of carbonyl compounds such as aldehydes and ketones with active methylene compounds to generate electrophilic alkenes. One of the most efficient carbon-carbon double bond formation methods in Knoevenagel condensation products have high reactivity and can be used in various chemical synthesis transformations. They are widely used in the synthesis of heterocyclic compounds, polymers, cosmetics and fragrances. The Knoevenagel condensation is a reaction in which a base is used as a catalyst and an organic solvent is used as a reaction medium. Commonly used homogeneous basic catalysts mainly include primary amines, secondary amin...

Claims

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Application Information

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IPC IPC(8): C07B43/08C07C255/34C07C253/30C07C255/35C07C255/42C07C255/37C07C255/40C07D307/54C07D213/57B01J31/02
Inventor 应安国胡华南邱方利魏文静武承林
Owner TAIZHOU UNIV
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