Method for producing acetophenone compound employing arylethynylene hydration reaction

A synthesis method and compound technology, applied in the preparation of carbon-carbon triple bond hydration, organic chemistry, etc., can solve problems such as environmental pollution, pollution, and intractability

Inactive Publication Date: 2015-04-08
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, heavy metal mercury salts are highly toxic, difficult to handle, and cause serious pollution to the environment.
At present, the hydration reaction

Method used

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  • Method for producing acetophenone compound employing arylethynylene hydration reaction
  • Method for producing acetophenone compound employing arylethynylene hydration reaction

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0024] Formation of acetophenone

[0025] Add 1 mmol of phosphorous acid into the reactor, then add 82 mg of water to prepare a 50% phosphorous acid aqueous solution, and then add 1 mmol of phenylacetylene. Heat to 80°C, keep stirring for 8h, stop the reaction, cool to room temperature, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product with a yield of 64%. 1 H NMR (400MHz, CDCl 3 , TMS): δ7.80 (d, J=7.60Hz, 2H), 7.40 (t, J=7.20Hz, 1H), 7.29 (t, J=7.60Hz, 2H), 2.43 (s, 3H).

[0026] Add the aqueous phase saved during the previous extraction step into the reactor, and then add 1 mL of an organic solvent (eg, n-hexane), and 1 mmol of phenylacetylene. Heat to 80°C, keep stirring for 15h, stop the reaction, cool to room temperature, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chrom...

Synthetic example 2

[0028] Formation of m-methylacetophenone

[0029] Add 1.2 mmol of phosphorous acid into the reactor, and then add 98.4 mg of water to prepare a 50% phosphorous acid aqueous solution, and then add 1 mmol of m-methylphenylacetylene. Heat to 100°C, keep stirring for 16h, stop the reaction, cool to room temperature, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product with a yield of 75%. 1 H NMR (400MHz, CDCl 3 , TMS): δ7.69 (s, 2H), 7.33–7.23 (m, 2H), 2.51 (s, 3H), 2.33 (s, 3H).

Synthetic example 3

[0031] Formation of p-methylacetophenone

[0032] Add 1.6 mmol of phosphorous acid into the reactor, and then add 131.2 mg of water to prepare a 131.2% phosphorous acid aqueous solution, and then add 1 mmol of p-methylphenylacetylene. Heat to 110°C, keep stirring for 12 hours, stop the reaction, cool to room temperature, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product with a yield of 69%. 1 H NMR (400MHz, CDCl 3 , TMS): δ7.75 (d, J=8.1Hz, 2H), 7.14 (d, J=8.0Hz, 2H), 2.46 (s, 3H), 2.30 (s, 3H).

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PUM

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Abstract

The invention provides a synthesis method of an acetophenone compound. The method comprises the following steps: by adopting mild, efficient, cheap and available phosphorous acid as a catalyst, and adopting water or organic solvent/water as a solvent by a reaction system, producing the acetophenone compound by taking phenylacetylene and derivatives thereof as reaction substances. The method has the advantages that the catalyst is cheap and available, and can be repeatedly utilized; the reaction system is an oil/water two-phase system; the obtained target product is easy to separate, relatively high in selectivity and productive rate, and mild in reaction condition; and the problems that a lewis acid catalyst is sensitive to water, and the product is not easy to separate and the like in the method for producing the acetophenone compound employing the phenylacetylene and the derivatives thereof are solved.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a method for generating acetophenone compounds through the hydration reaction of aryl alkynes. 【Background technique】 [0002] The hydration reaction of alkynes to form carbonyl compounds is one of the most important and basic methods for functional group transformation in organic synthesis. [0003] The traditional alkyne hydration reaction is generally carried out in an organic solvent such as methanol with a strong acid as a catalyst, in order to improve the conversion rate of the reaction. Add Hg to the reaction system 2+ Salt. However, heavy metal mercury salts are highly toxic, difficult to handle, and cause serious pollution to the environment. At present, the hydration reaction of phenylacetylene in aqueous medium adopts homogeneous catalysts, but homogeneous catalysts are difficult to reuse and cause environmental pollution. [0004] In view of the shortcomings of ...

Claims

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Application Information

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IPC IPC(8): C07C45/26C07C49/78C07C49/76C07C49/84C07C49/807C07C49/825
CPCC07C45/26
Inventor 周永波李妹刘妍希李中文尹双凤陈秀玲韩立彪
Owner HUNAN UNIV
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