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Method for synthesizing alkene ester

A technology of enesters and reactants, which is applied in the field of chemical synthesis, can solve problems such as difficulty in large-scale industrial production, narrow application range, and low atom economy, and achieve high yield, wide application range, and high atom economy. Effect

Inactive Publication Date: 2015-01-07
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The former method requires the use of metal catalysts, a large number of ligands or additives, low selectivity, and narrow application range, so it is not an optimal synthetic route
[0003] However, the only report on the Baeyer Villiger oxidation of α, β-unsaturated ketones to prepare enesters uses inorganic peroxide salts as oxidants, which will generate a large amount of solid waste after the reaction, and the atom economy is low, making it difficult to apply to large-scale industrial production.
And the scope of application is narrow, limited to the synthesis of vinyl acetate
[0004] Currently, there is a lack of a high-yield, atom-economical synthesis of enesters

Method used

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  • Method for synthesizing alkene ester
  • Method for synthesizing alkene ester
  • Method for synthesizing alkene ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]

[0018] 1 mmol α, β-unsaturated ketone, 4 mmol hydrogen peroxide (30 w / w%), 0.05 mmol dibenzyl diselenide were stirred in 2 ml acetonitrile at room temperature (25° C.). After 24 hours, the reaction was completed, evaporated to dryness with a rotary evaporator, and the residue was separated by preparative wave chromatography to obtain the enester.

[0019] Check the application range of the reaction substrate, as shown in Table 1, the experimental results of the inspection of the substrate application range.

[0020] Table 1

[0021]

[0022] Note: Yields are isolated yields. From the above results, it can be seen that this reaction has a wide range of applications and is suitable for the synthesis of various enesters.

Embodiment 2

[0024] Other conditions are the same as in Example 1, No. 1. Different volumes of acetonitrile solvents were used, as shown in Table 2 for the experimental results of different volumes of acetonitrile solvents.

[0025] Table 2

[0026]

[0027] Note: The GC yields are outside the brackets, and the separation yields are inside the brackets. As can be seen from the above, the initial reactant concentration is between 0.1-1mol / l, and wherein the effect of the production rate with the initial reactant concentration in No. 1 being 0.5mol / l is the best in Example 1.

Embodiment 3

[0029] Other conditions are the same as embodiment 1, No. 1. Test the reaction using different catalysts, such as Table 3 is the experimental results of the test of different catalysts.

[0030] table 3

[0031] Numbering

[0032] 19

[0033] Note: The GC yields are outside the brackets, and the separation yields are inside the brackets. From the above results, it can be seen that diselenide and organic selenous acid have the best effect, and wherein the yield of dibenzyl diselenide in No. 1 in Example 1 is the best effect.

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PUM

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Abstract

The invention discloses a method for synthesizing alkene ester. The method comprises the following step: by using organic diselenide or organic seleninic acid as a catalyst and hydrogen peroxide as an oxidizing agent, carrying out catalytic oxidation on a reactant alpha, beta-unsaturated ketone to prepare alkene ester in an acetonitrile solvent at the reaction temperature of 0-60 DEG C, wherein the reactant concentration is 0.1-1mol / l, the use level of the catalyst is 0.5-10mol% of the reactant, and the use level of hydrogen peroxide is 120-500mol%. The method disclosed by the invention is energy-saving and environment-friendly, easily available in raw materials, high in yield, mild in reaction condition, high in reaction selectivity and atom economy and more suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing enesters. Background technique [0002] Enyl esters are important organic compounds and are widely used in organic synthesis, medicinal chemistry, material chemistry, and food chemistry. At present, there are two main methods for the synthesis of enesters, one is through the catalytic addition of alkynes to carboxylic acids or the oxidative coupling of alkenes to carboxylic acids; the other is through the Baeyer Villiger reaction of α,β-unsaturated ketones. oxidation reaction. The former method requires the use of metal catalysts, a large number of ligands or additives, low selectivity, and narrow application range, therefore, it is not an optimal synthetic route. [0003] However, the only report on the Baeyer Villiger oxidation of α, β-unsaturated ketones to prepare enesters uses inorganic peroxide salts as oxidants, which will generate a large amou...

Claims

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Application Information

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IPC IPC(8): C07C67/42C07C69/157C07C69/16C07C69/21C07C69/63C07C69/145C07C69/24C07C69/78C07C69/767C07C69/92
CPCC07C67/42C07C2601/16C07C69/157C07C69/63C07C69/16C07C69/21C07C69/24C07C69/78C07C69/145C07C69/76C07C69/92
Inventor 俞磊黄亚萍叶剑青张旭丁克鸿徐清
Owner YANGZHOU UNIV
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