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Method used for direct synthesis of epoxy compounds from alcohol

An epoxy compound and synthesis method technology, applied in the directions of organic chemistry, bulk chemical production, etc., can solve the problems of difficult treatment process, harsh operating conditions, large three-waste discharge, etc., and achieves cheap and easy-to-obtain reaction reagents and easy preparation process. Controls, substrates for a wide range of effects

Active Publication Date: 2019-09-27
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of olefins often requires multi-step reactions, the preparation process is cumbersome, the process is long, the control process is difficult, and the three wastes are discharged. In particular, the preparation of olefin compounds with complex structures is more difficult, with low yield and low purity.
[0004] The Chinese invention patent with the application number 2018102226848 discloses a method for synthesizing epoxides, which uses hydrogen peroxide as the oxidant to catalyze epoxides containing carbon-carbon double bonds and at least one other functional group in a catalytic system composed of a catalyst and a solvent. The reactants synthesize epoxides, the solvent in the catalytic system is a mixture of alcohol and water, and the catalyst is a mixture of metal ion-modified titanium-silicon molecular sieves with a MWW structure and a carrier; although the target epoxide is synthesized in this reaction, the The steps are cumbersome, the operating conditions are harsh, and a catalyst is required, making the post-treatment process difficult

Method used

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  • Method used for direct synthesis of epoxy compounds from alcohol
  • Method used for direct synthesis of epoxy compounds from alcohol
  • Method used for direct synthesis of epoxy compounds from alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 A kind of method of directly synthesizing epoxy compound 1 by alcohol

[0037] (11) Dissolve 1.1 mmol of oxalyl chloride in 1 mL of anhydrous dichloromethane at -78°C in a nitrogen atmosphere, slowly add 2.2 mmol of anhydrous dimethyl sulfoxide dropwise to the reaction system, and stir for 30 minutes to obtain A1;

[0038] (12) Dissolve 1.1 mmol of 4-(hydroxymethyl) methyl benzoate in 0.5 mL of anhydrous dichloromethane, slowly add it dropwise to A1, stir for 2.5 h, and slowly add 5.5 mmol of triethylamine to the reaction system, Stir for 1h to obtain B1;

[0039] (13) TLC (thin layer chromatography) detection, the raw materials disappeared, the reaction was moved to room temperature, and 1.1mmol 4-tert-butylbenzyl bromide, 5.5mmol lithium hydroxide, 0.2mL water and 0.5mL were added to B1 at room temperature Dimethyl sulfoxide, reacted at 20°C for 12 hours, detected by TLC (thin layer chromatography), the raw material point disappeared, and the reaction wa...

Embodiment 2

[0044] Embodiment 2 A kind of method of directly synthesizing epoxy compound 2 by alcohol

[0045] (21) Dissolve 1.1 mmol of acetic anhydride in 1 mL of anhydrous dichloromethane at -70°C in a nitrogen atmosphere, slowly add 5.5 mmol of anhydrous dimethyl sulfoxide dropwise to the reaction system, and stir for 50 min to obtain A2;

[0046] (22) Dissolve 1.1mmol of 4-cyanobenzyl alcohol in 0.5mL of anhydrous dichloromethane, slowly add it dropwise to A2, stir for 1h, slowly add 8.8mmol of triethylamine to the reaction system, stir for 1h, and obtain B2 ;

[0047] (23) TLC (thin-layer chromatography) detection, the raw materials disappeared, the reaction was moved to room temperature, and 1.1mmol 4-tert-butylbenzyl bromide, 7.7mmol cesium carbonate, 0.2mL water and 0.5mL tert-butylbenzyl bromide were added to B2 at room temperature Butanol, reacted at 35°C for 15h, detected by TLC (thin layer chromatography), the raw material point disappeared, and the reaction was stopped to o...

Embodiment 3

[0052] Embodiment 3 A kind of method of directly synthesizing epoxy compound 3 by alcohol

[0053] (31) Dissolve 2.2 mmol of acetic anhydride in 1 mL of anhydrous dichloromethane at -60°C in a nitrogen atmosphere, slowly add 3.3 mmol of anhydrous dimethyl sulfoxide dropwise to the reaction system, and stir for 10 min to obtain A3;

[0054] (32) Dissolve 1.1mmol of 4-tert-butylbenzyl alcohol in 0.5mL of anhydrous dichloromethane, slowly add it dropwise to A3, stir for 1.5h, slowly add 3.3mmol of DBU to the reaction system, stir for 2.5h to obtain B3 ;

[0055] (33) TLC (thin layer chromatography) detects that the raw material disappears, and the reaction is moved to room temperature, and 1.1 mmol 4-methyl-2,3,5,6-tetrafluoro-benzyl bromide is added to B3 at room temperature, 8.8 Mmol sodium carbonate, 0.2mL water and 0.5mL isopropanol were reacted at 35°C for 20h, detected by TLC (thin layer chromatography), the starting point disappeared, and the reaction was stopped to obtai...

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Abstract

The invention discloses a method used for direct synthesis of an epoxy compounds from an alcohol. According to the method, an alcohol is taken as a raw material, Swern oxidation is adopted to synthesize an aldehyde, a bromo-hydrocarbon and an alkali are added into the aldehyde directly to construct epoxy functional groups, and generate the epoxy compound. According to the method, one-pot method is adopted to realize direct epoxidation of the alcohol, the synthesis route is simple, the preparation process is easy to control, no catalyst is needed in the process, substrate suitable range is wide, reagents are cheap and easily available, preparation conditions are mild, reaction yield is high, and the method is suitable for synthesis of epoxy compounds.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a method for directly synthesizing epoxy compounds from alcohols. Background technique [0002] Epoxy functional group is an oxygen-containing three-membered ring that widely exists in natural products and bioactive molecules. For example, triptolide, epothilone A, crotonepoxide, etc. all contain epoxy functional groups. Epoxy functional groups can synthesize many intermediates through chemical transformation. At the same time, epoxy compounds are widely used in detergents, lubricating oils, textiles and cosmetics, so the research on the synthesis of epoxy compounds is of great significance. [0003] At present, the method for synthesizing epoxy compounds is mainly the epoxidation of olefins, such as Sharpless epoxidation, Jacobsen / Katsuki epoxidation, Shi-An epoxidation, etc. However, the synthesis of olefins often requires multi-step reactions, the preparation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/02C07D303/40C07D303/38C07D303/08C07D303/22C07D405/04C07D303/04
CPCC07D301/02C07D303/40C07D303/38C07D303/08C07D303/22C07D405/04C07D303/04Y02P20/52
Inventor 张志伟李海波刘守信王翠翠李军章冯娟
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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