Method for using deep eutectic solvent for preparing 2-(4-chlorphenyl-hydroxyl methyl)-acrylonitrile

A technology of deep eutectic solvent and hydroxymethyl group is applied in the field of preparation of multifunctional compounds, which can solve the problems of environmental pollution and economic benefits, and achieve the effects of simple post-reaction treatment, high reaction yield and shortened reaction time.

Inactive Publication Date: 2016-05-11
XINZHOU TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the invention is to solve the technical problems of environmental pollution and poor economic benefit in the preparation method of existing 2-(4-chlor

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] A method for preparing 2-(4-chlorophenyl-hydroxymethyl)-acrylonitrile using a deep eutectic solvent in this embodiment is made by the following steps:

[0013] 1) Preparation of a deep eutectic solvent: Mix 5 g of choline chloride and 3.3 g of glycerol, and stir magnetically at a constant temperature at 85° C. for 8 hours to obtain a deep eutectic solvent;

[0014] 2) Preparation of composite solvent: mix 3 g of the deep eutectic solvent prepared in step 1) with 1 g of water evenly to obtain a composite solvent;

[0015] 3) Preparation of 2-(4-chlorophenyl-hydroxymethyl)-acrylonitrile: 3g of the composite solvent prepared in step 2), 0.7g of chlorobenzaldehyde, 0.4g of acrylonitrile and 1g of 1,4-diazabis Add cyclo[2.2.2]octane to the reaction vessel, stir magnetically at 20°C for 60 minutes, filter the solid product in the reaction system, remove the filtrate, and wash the filter cake twice with water, and place the washed filter cake under vacuum After drying for 1 h...

Embodiment 2

[0017] A method for preparing 2-(4-chlorophenyl-hydroxymethyl)-acrylonitrile using a deep eutectic solvent in this embodiment is made by the following steps:

[0018] 1) Preparation of a deep eutectic solvent: Mix 5 g of choline chloride and 9.9 g of glycerol, and stir magnetically at a constant temperature at 95° C. for 12 hours to obtain a deep eutectic solvent;

[0019] 2) Preparation of composite solvent: mix 6 g of the deep eutectic solvent prepared in step 1) with 3 g of water evenly to obtain a composite solvent;

[0020] 3) Preparation of 2-(4-chlorophenyl-hydroxymethyl)-acrylonitrile: 5g of the composite solvent prepared in step 2), 0.7g of chlorobenzaldehyde, 0.4g of acrylonitrile and 1g of 1,4-diazabis Add cyclo[2.2.2]octane to the reaction vessel, stir magnetically at 25°C for 100 min, filter the solid product in the reaction system, remove the filtrate, and wash the filter cake twice with water, and place the washed filter cake under vacuum After drying for 5 hou...

Embodiment 3

[0022] A method for preparing 2-(4-chlorophenyl-hydroxymethyl)-acrylonitrile using a deep eutectic solvent in this embodiment is made by the following steps:

[0023] 1) Prepare a deep eutectic solvent: mix 5 g of choline chloride and 6.6 g of glycerol, and stir magnetically at a constant temperature at 90° C. for 10 hours to obtain a deep eutectic solvent;

[0024] 2) Preparation of composite solvent: Mix 3 g of the deep eutectic solvent prepared in step 1) with 1.3 g of water evenly to obtain a composite solvent;

[0025] 3) Preparation of 2-(4-chlorophenyl-hydroxymethyl)-acrylonitrile: 4g of the composite solvent prepared in step 2), 0.7g of chlorobenzaldehyde, 0.4g of acrylonitrile and 1g of 1,4-diazabis Add cyclo[2.2.2]octane to the reaction vessel, stir magnetically at 23°C for 80 minutes, filter the solid product in the reaction system, remove the filtrate, and wash the filter cake twice with water, and place the washed filter cake under vacuum After drying for 3 hours...

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Abstract

The invention belongs to the technical field of preparing methods of polyfunctional group compounds and particularly relates to a method for using deep eutectic solvent for preparing 2-(4-chlorphenyl-hydroxyl methyl)-acrylonitrile. The method mainly solves the problems that when an existing method for preparing 2-(4-chlorphenyl-hydroxyl methyl)-acrylonitrile is used, environment is polluted, and economic benefits are poor. According to the method, choline chloride and glycerin are mixed according to a certain ratio at the temperature of 95 DEG C to prepare the deep eutectic solvent, and then the deep eutectic solvent and water are combined according to the ratio to prepare complex solvent. As the raw materials used for preparing the complex solvent are compounds free of toxicity or low in toxicity, the compound solvent is an environment-friendly medium. The compound solvent is used as a reaction medium and applied to a Morita-Baylis-Hillman (M-B-H) reaction of p-chlorobenzaldehyde and acrylonitrile, wherein DABCO is used for catalyzing the M-B-H reaction, the reaction yield is up to 95%, reaction time is shortened greatly to be a few minutes, most importantly, treatment after the reaction is easy, and a pure target product can be obtained just by simple filtering and washing.

Description

technical field [0001] The invention belongs to the technical field of preparation methods of multifunctional compounds, and in particular relates to a method for preparing 2-(4-chlorophenyl-hydroxymethyl)-acrylonitrile using a deep eutectic solvent. Background technique [0002] 2-(4-Chlorophenyl-hydroxymethyl)-acrylonitrile is a multifunctional compound, which contains not only functional groups that can be further transformed, such as halogen atoms, hydroxyl groups, and cyano groups, but also double bonds and aromatic rings. Important organic synthesis intermediates. The synthesis of this compound is generally catalyzed by a catalyst, especially 1,4-diazabicyclo[2.2.2]octane (DABCO), through Morita–Baylis-Hillman (M-B-H) of p-chlorobenzaldehyde and acrylonitrile The response is realized. This reaction has significant advantages, such as good reaction selectivity, mild reaction conditions, and all the raw material molecules participating in the reaction are included in t...

Claims

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Application Information

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IPC IPC(8): C07C255/36C07C253/30
CPCC07C253/30C07C255/36
Inventor 赵三虎张婷任海仙郭瑾昌
Owner XINZHOU TEACHERS UNIV
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