Method for prepring compound of beta hydroxyketone in supercritical liquid of carbon dioxide

A technology of carbon dioxide and compounds, applied in the field of preparation of β-hydroxy ketone compounds in supercritical carbon dioxide fluid, to achieve the effect of overcoming environmental pollution, reducing pollution, and reducing environmental pollution

Inactive Publication Date: 2007-12-26
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is to overcome the shortcoming of the above-mentioned

Method used

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  • Method for prepring compound of beta hydroxyketone in supercritical liquid of carbon dioxide
  • Method for prepring compound of beta hydroxyketone in supercritical liquid of carbon dioxide
  • Method for prepring compound of beta hydroxyketone in supercritical liquid of carbon dioxide

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Taking the raw material p-nitrobenzaldehyde 0.5g used for the preparation of 4-(4-nitrophenyl)-4-hydroxyl-2-butanone as an example, other raw materials used and the process steps are as follows:

[0021] 1. Preparation of crude β-hydroxy ketone compound

[0022] Add acetone 5.76g and p-nitrobenzaldehyde 0.5g in the supercritical autoclave, the molar ratio of p-nitrobenzaldehyde 0.5g and acetone is 1:30, add catalyst L-proline 0.057g, p-nitrobenzaldehyde The molar ratio of benzaldehyde to L-proline is 1:0.15, the reaction kettle is sealed, and CO is filled with a high-pressure micro-injection pump. 2 Fill the liquid to a pressure of 35MPa and react at 50°C for 30 hours. The chemical reaction equation is as follows:

[0023]

[0024] After the reaction is complete, CO is released 2 , add ethyl acetate to the reaction kettle until the reaction product dissolves, take out the solution, filter to remove the catalyst L-proline, and use a rotary evaporator to evaporate th...

Embodiment 2

[0028] Taking the raw material p-nitrobenzaldehyde 0.5g used for the preparation of 4-(4-nitrophenyl)-4-hydroxyl-2-butanone as an example, other raw materials used and the process steps are as follows:

[0029] In the preparation of β-hydroxy ketone compound crude product process step 1, add acetone 1.92g and p-nitrobenzaldehyde 0.5g in the supercritical autoclave, the mol ratio of p-nitrobenzaldehyde 0.5g and acetone is 1: 10, Add 0.114 g of catalyst L-proline, the molar ratio of p-nitrobenzaldehyde to L-proline is 1:0.3, seal the reaction kettle, and fill it with CO 2 The liquid was charged to a pressure of 20MPa, and reacted at 60°C for 15 hours. Other steps in this processing step are identical with embodiment 1.

[0030] Other steps are the same as in Example 1.

Embodiment 3

[0032] Taking the raw material p-nitrobenzaldehyde 0.5g used for the preparation of 4-(4-nitrophenyl)-4-hydroxyl-2-butanone as an example, other raw materials used and the process steps are as follows:

[0033] In the preparation of β-hydroxy ketone compound crude product process step 1, add acetone 3.84g and p-nitrobenzaldehyde 0.5g in the supercritical autoclave, the molar ratio of p-nitrobenzaldehyde and acetone is 1: 20, add catalyst L-proline 0.02g, the molar ratio of p-nitrobenzaldehyde and L-proline is 1: 0.05, seal the reaction kettle, fill with CO 2 The liquid was filled to a pressure of 10MPa, and reacted at 30°C for 36 hours. Other steps in this processing step are identical with embodiment 1.

[0034] Other steps are the same as in Example 1.

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Abstract

This invention discloses a method for preparing beta-hydroxy ketones in supercritical CO2 fluid. The method comprises: preparing crude beta-hydroxy ketone compounds, separating and purifying. The method performs asymmetric aldol condensation reaction on acetone and different aldehyde compounds catalyzed by L-proline in supercritical CO2 fluid. The method solves the problems serious environmental pollution and complex post treatment faced by traditional organic solvent method. The method has such advantages as no need for organic solvent, little environmental pollution, high productivity and high enantio selectivity of the catalyst. The proton NMR spectrum of the product is identical to that of 4-(4-nitrophenyl)-4-hydroxyl-2-butanone. The method has such advantages as reasonable design, simple process, little pollution, high yield, and high enantio selectivity of the catalyst.

Description

technical field [0001] The invention belongs to the technical field of synthesizing organic intermediate materials such as β-hydroxy ketones, α, β-unsaturated carbonyl compounds and 1,2-diol, and specifically relates to a preparation method of β-hydroxy ketone compounds in supercritical carbon dioxide fluid. Background technique [0002] Chiral β-hydroxyketones are important intermediates in the asymmetric synthesis of many natural products. Carbonyl and hydroxyl groups are reactive groups that can be converted into vicinal diols, β-amino ketones, and other functional groups. [0003] Aldol condensation reaction is an important reaction to form carbon-carbon bonds, which can be used to synthesize organic compounds such as β-hydroxy ketones, α, β-unsaturated carbonyl compounds and 1,2-diols. In the synthesis of natural products, asymmetric aldol condensation reaction has been widely used. [0004] The industrial process for the aldol condensation of aldehydes and ketones to...

Claims

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Application Information

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IPC IPC(8): C07C45/72C07C205/45C07C49/245C07C49/255
CPCY02P20/54
Inventor 刘昭铁刘玲刘忠文
Owner SHAANXI NORMAL UNIV
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