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Method for preparation of 9-aryl-2, 3, 4, 5, 6, 7-hexahydro-2H-xanthene-1, 8-dione without catalyst

A catalyst, xanthene technology, applied in the direction of organic chemistry, etc., can solve the problems of not having large-scale industrial application, corrosion of equipment, complicated operation process, etc., and achieve the benefits of large-scale industrial production, lower production costs, and wide sources of raw materials Effect

Inactive Publication Date: 2017-04-26
王俊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the above methods have one or more of the following disadvantages: longer reaction time; lower yield; higher catalyst cost; catalyst cannot be recycled; use volatile organic solvents; It can be suitable for laboratory or small-scale operations, and does not have large-scale industrial applications, etc.

Method used

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  • Method for preparation of 9-aryl-2, 3, 4, 5, 6, 7-hexahydro-2H-xanthene-1, 8-dione without catalyst
  • Method for preparation of 9-aryl-2, 3, 4, 5, 6, 7-hexahydro-2H-xanthene-1, 8-dione without catalyst

Examples

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Embodiment 1

[0021] In a 25mL round-bottom flask, add 10 mmol (1.06g) benzaldehyde, 20 mmol (2.24g) 1,3-cyclohexanedione, 5g glycerol in turn, mix and stir at 92°C for 2.0 hours under normal pressure, add 10mL water , let it cool down. Filtration and washing with cold water, recrystallization from 95% ethanol gave the pure product of 9-phenyl-2,3,4,5,6,7-hexahydro-2H-xanthene-1,8-dione, yield 81 %.

Embodiment 2

[0023] In a 25mL round bottom flask, add 10 mmol (1.51 g) of 4-nitrobenzaldehyde, 20 mmol (2.24 g) of 1,3-cyclohexanedione, and 6 g of glycerol in sequence, and mix and stir at 90°C for 2.5 hours under normal pressure , add 10mL of water, let stand to cool. Filtered and washed with cold water, recrystallized from 95% ethanol to obtain the pure product of 9-(4-nitrophenyl)-2,3,4,5,6,7-hexahydro-2H-xanthene, yield 78% .

Embodiment 3

[0025] In a 25mL round bottom flask, add 10 mmol (1.51 g) of 3-nitrobenzaldehyde, 20 mmol (2.24 g) of 1,3-cyclohexanedione, and 6 g of glycerol in sequence, and mix and stir for 2.5 hours at 90°C under normal pressure , add 10mL of water, let stand to cool. Filtered and washed with cold water, recrystallized from 95% ethanol to obtain the pure product of 9-(3-nitrophenyl)-2,3,4,5,6,7-hexahydro-2H-xanthene, the yield was 82% .

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Abstract

Belonging to the technical field of chemical material preparation, the invention provides a method for synthesis of 9-aryl-2, 3, 4, 5, 6, 7-hexahydro-2H-xanthene-1, 8-dione without catalyst. The method includes: carrying out condensation reaction on aromatic aldehyde and 1, 3-cyclohexanedione in a mole ratio of 1:2 without any catalyst at 90-92DEG C for 1.5-2.5h, taking glycerin accounting for 59%-81% of the total material mass as the reaction medium, at the end of the reaction adding water for cooling standing, and performing filtering to obtain a crude solid product, washing the crude product, then conducting recrystallization with 95% ethanol, thus obtaining a pure product. Filtrate is distilled to remove water, and the recycled glycerin can be reused. Compared with the traditional preparation method using acid, alkali and ionic liquid as the catalyst, the method provided by the invention does not need any catalyst, and has the advantages of simplicity, low cost, green and environmental protection, and is beneficial to large-scale industrial production, etc.

Description

technical field [0001] The invention relates to a method for preparing 9-aryl-2,3,4,5,6,7-hexahydro-2H-xanthene-1,8-dione, which belongs to the technical field of chemical material preparation. This method is suitable for the synthesis of 9-aryl-2,3,4,5,6,7-hexahydro-2H-oxanthene-1,8- Diketones. Background technique [0002] Many organic compounds containing pyran rings have important biological and pharmacological activities, such as anti-cancer, anti-allergic, anti-dysplasia and anti-hypertension. Xanthenediones have a pyran ring structure and are the structural units of many natural medicines, as well as important intermediates for the synthesis of other heterocyclic compounds. In addition, because of its unique fluorescence spectral characteristics, it is widely used in biomolecular perspective and laser technology. [0003] Based on the unique physiological activity of xanthenediones, they are widely used, and the research on these compounds is constantly developing....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82
CPCC07D311/82
Inventor 王俊李乐周舟陶建清薛云珊吉海峰王岩方东
Owner 王俊