Efficient catalysis method for Knoevenagel condensation reaction

A condensation reaction, high-efficiency technology, used in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, preparation of organic compounds, etc. problem, to achieve the effect of efficient catalytic condensation reaction and simple material recovery

Active Publication Date: 2022-08-09
ZHONGYUAN ENGINEERING COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some Knoevenagel condensation reactions promoted by solid-phase resins have low yields and produce by-products, and post-processing is also very inconvenient
Some examples of no catalyst or special catalyst, most of the conditions are strict and the applicability is not wide

Method used

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  • Efficient catalysis method for Knoevenagel condensation reaction
  • Efficient catalysis method for Knoevenagel condensation reaction
  • Efficient catalysis method for Knoevenagel condensation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthetic method of tetrahydroxytetraaldehyde tetraphenylene is as follows:

[0034]

[0035] In a 500mL three-necked flask, firstly add the weighed zinc powder (35.9g, 553.31mmol) and a stirring magnet, sort out the brine sealing system, set up a reflux condensing device, and then repeat the vacuum evacuation and fill with nitrogen three times. Add 190 mL of freshly purified anhydrous tetrahydrofuran (THF) with a standard syringe, cool it to 0°C under an ice-water bath, and then slowly add a quantitative amount of titanium tetrachloride (30.0 mL, 280.08 mmol) with a syringe of suitable size, inject After the end, continue to stir in an ice-water bath for about 15 minutes, then heat and reflux for 3.0h, after that, stop heating and let the reaction system cool to room temperature, then slowly add quantitative 4,4-dihydroxydiphenyl using a constant pressure dropping funnel A solution of methyl ketone (9.1 g, 42.01 mmol) dissolved in 100 mL of anhydrous THF (tetrah...

Embodiment 2

[0037] The synthesis method of the catalyst for the Knoevenagel condensation reaction is as follows:

[0038] Accurately weigh 5 mg of tetrahydroxytetraaldehyde tetraphenylethylene, 5 μL of ethylenediamine, 1.5 mL of 1,4 dioxane, Zn(OAC) 2 ·2H 2 O 20.8 mg, 0.2 mL of 3M aqueous glacial acetic acid. Put the weighed medicine into a prepared glass bottle that can withstand high temperature and low temperature at the same time, freeze, thaw, and reciprocate three times under the conditions of liquid nitrogen cooling and oil pump vacuuming. The tube was sealed with a flame gun, the sealed glass bottle was put into a beaker, and the beaker was put into an oven at 120° C. to react for 72 hours.

[0039] Three days later, take out the glass tube, open the seal, take out the solid insoluble matter, and slowly wash it on a separatory funnel with the large polar solvent tetrahydrofuran, DMF, and methanol. After that, the product was put into a vacuum oven at 60 °C for one day and one n...

Embodiment 3

[0043] An efficient catalytic method for Knoevenagel condensation reaction, using acetonitrile as a solvent, in the presence of the catalyst prepared in Example 2, the reaction temperature of aldehyde and malononitrile is 60°C, and the reaction time is 15 minutes.

[0044] 1. The best solvent for COFs to catalyze the Knoevenagel condensation reaction

[0045]Take four dry test tubes and number them ①②③④. Add COF-Zn (5mg), ultra-dry methanol (1mL) and p-chlorobenzaldehyde (20mg) to the test tube No. 1 in turn, and add COF-Zn (5mg) to the test tube No. , p-chlorobenzaldehyde (20mg), malononitrile (100mg) and 1,2 dichloromethane (1mL), 5mgCOF-Zn + p-chlorobenzaldehyde (20mg) + malononitrile (100mg) + acetonitrile were added to the test tube No. (0.1 mL), 5 mg of COF-Zn + p-chlorobenzaldehyde (20 mg) + malononitrile (100 mg) + 1,4 dioxane (0.1 mL) were added to the test tube No. 4 in turn. Put the four test tubes into a constant temperature magnetic stirrer with a temperature of ...

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Abstract

The invention discloses an efficient catalysis method for a Knoevenagel condensation reaction, which comprises the following steps: by taking acetonitrile as a solvent, reacting aldehyde and malononitrile at the temperature of 60 DEG C for 15 minutes in the presence of a catalyst; the structural formula of the catalyst is shown in the specification. The novel COFs complex zinc material used in the invention can realize efficient catalysis, and the reaction is complete at room temperature within 15 minutes. The material is easy to recycle and can be filtered and washed. An organic part is Schiff base and is a very good organic weak base, and complexed metal zinc is used as inorganic base to efficiently catalyze condensation reaction.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a high-efficiency catalytic method for Knoevenagel condensation reaction. Background technique [0002] Covalent organic frameworks (COFs) are a kind of organic porous materials, which are polymers with a network structure composed of interconnected or closed nano-holes, because of their large specific surface area and relatively low density, Therefore, it has good applications in gas storage and separation, heterogeneous catalysis, photovoltaic power generation and other fields. COFs materials are crystalline porous materials formed by covalent bonding of organic building blocks. COFs materials have outstanding performance in terms of thermal stability and chemical stability, so they have a broader platform for applications. The COFs material itself has the characteristics of crystallinity and porosity, the pores are regular and orderly, the pore size can be expanded ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/54C07C253/30C07C255/34B01J31/22
CPCC07D307/54C07C253/30B01J31/2213B01J31/1691B01J2531/26C07C255/34Y02P20/584
Inventor 熊加斌班丁丁
Owner ZHONGYUAN ENGINEERING COLLEGE
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