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Catalytic system for synthesizing alpha-hydroxy ketone by alkynol hydration reaction

A catalytic system, acetylenic alcohol hydration technology, applied in the direction of organic compound/hydride/coordination complex catalyst, carbon-carbon triple bond hydration preparation, physical/chemical process catalyst, etc., can solve rearrangement and other problems, and achieve high Catalytic activity, easy synthesis and recovery, wide range of effects

Active Publication Date: 2015-03-25
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above catalytic systems usually require strong acids or bases and organic ligands, etc., and side reactions such as Meyer-Schuster and Rupe rearrangements may occur

Method used

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  • Catalytic system for synthesizing alpha-hydroxy ketone by alkynol hydration reaction
  • Catalytic system for synthesizing alpha-hydroxy ketone by alkynol hydration reaction
  • Catalytic system for synthesizing alpha-hydroxy ketone by alkynol hydration reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1. Catalyzing the hydration reaction of 2-methyl-3-butyn-2-ol to generate 3-hydroxyl-3-methyl-2-butanone

[0024] In a 250 ml single-necked bottle, 2-methyl-3-butyn-2-ol (8.41 g, 0.1 mol), H 2 O (3.60g, 0.2mol) and formula I a [Bu 4 P][Im] (97.89g, 0.3mol), with CO 2 displace the air therein; then keep the CO 2 The pressure was 0.1MPa, refluxed and stirred at 80°C for 24 hours. After the reaction is finished, with tert-butanol as internal standard, by 1 H NMR quantitative detection, using the conventional internal standard method for calculation, the yield of 3-hydroxy-3-methyl-2-butanone was 90%.

[0025] reaction product 1 H and 13 C nuclear magnetic spectrum to determine its structure:

[0026] 1 H NMR (DMSO-d6, 400 MHz) δ 5.21 (s, 1H), 2.15 (s, 3H), 1.17 (s, 6H).

[0027] 13 C NMR (DMSO-d 6 , 100MHz) δ213.64, 75.76, 26.15, 24.11.

[0028] It can be seen from the above that the product has a correct structure and is 3-hydroxy-3-methyl-2-butanone....

Embodiment 2

[0029] Example 2, catalyzing the hydration reaction of 2-methyl-3-butyn-2-ol to generate 3-hydroxyl-3-methyl-2-butanone

[0030] Adopt exactly the same reaction condition and detection method as embodiment 1, only [Bu 4 The amount of P][Im] was changed to 163.15g (0.5mol), and the yield of 3-hydroxyl-3-methyl-2-butanone was 88%.

Embodiment 3

[0031] Example 3, catalyzing the hydration reaction of 2-methyl-3-butyn-2-ol to generate 3-hydroxy-3-methyl-2-butanone

[0032] Adopt exactly the same reaction condition and detection method as embodiment 1, only [Bu 4 P][Im] amount is changed into 65.26g (0.2mol), CO 2 The gas pressure was changed to 1 MPa, the reaction time was changed to 24 h, and the yield of 3-hydroxy-3-methyl-2-butanone was 86%.

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Abstract

The invention discloses a catalytic system for synthesizing alpha-hydroxy ketone by alkynol hydration reaction. The catalytic system consists of an ionic liquid and a CO2 gas, wherein the ionic liquid is selected from at least one of ionic liquids as shown in formulas Ia-Ie described in the specification. In the catalytic system, the amount of substances of the ionic liquid is 0.01-0.5mol, and the pressure of the gas is 0.1-8MPa. The invention further provides a method of preparing alpha-hydroxy ketone compounds by utilizing the catalytic system. The catalytic system is suitable for a reaction system for catalyzing alkynol hydration reaction to synthesize alpha-hydroxy ketone compounds. The catalytic system is relatively high in catalytic activity, mild in reaction condition, and free of metals. The main catalyst ionic liquid is easy to synthesize and recycle, and has a relatively strong application value.

Description

technical field [0001] The invention belongs to the field of catalysts, and in particular relates to a catalytic system for synthesizing α-hydroxy ketones through the hydration reaction of acetylenic alcohols. Background technique [0002] α-Hydroxyketones are a very important class of organic compounds, which widely exist in the molecular framework of biologically active compounds and synthetic drugs (Y.F.Liang, N.Jiao, Angew.Chem.Int.Ed.2014,53,548) ; Therefore, it is of great significance to develop methods and catalytic systems for the efficient synthesis of α-hydroxy ketones. [0003] The hydration reaction of acetylenic alcohols is a simple and atom-economical method for the synthesis of α-hydroxy ketones, which meets the requirements of green chemistry and sustainable development. At present, a variety of metal catalysts, such as platinum (Pt), gold (Au), silver (Ag), etc. have been developed to replace the traditional toxic mercury (Hg) catalytic system for the hydr...

Claims

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Application Information

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IPC IPC(8): B01J31/02B01J31/04C07C45/26C07C49/17C07C49/245C07C49/337
Inventor 赵燕飞刘志敏杨珍珍于博张宏晔杨冠英
Owner INST OF CHEM CHINESE ACAD OF SCI
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