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Method for preparing xanthene amerantrone derivative via catalysis of acidic ionic liquid

An acidic ionic liquid, xanthene dione technology, applied in chemical recovery, organic chemistry and other directions, can solve the problems of large loss of catalyst usage, harsh reaction conditions, environmental pollution, etc., and achieve less catalyst usage and catalytic efficiency. The effect of reducing and good catalytic activity

Inactive Publication Date: 2013-07-10
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to overcome the shortcomings of the prior art, such as serious environmental pollution, harsh reaction conditions, large amount of catalyst usage and loss in recycling, and provide a catalytic preparation of xanthene diketones by acidic ionic liquids. Derivative method

Method used

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  • Method for preparing xanthene amerantrone derivative via catalysis of acidic ionic liquid

Examples

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Effect test

Embodiment 1

[0018] Add 10mmol of benzaldehyde, 20mmol of 1,3-cyclohexanedione, 15mL of absolute ethanol and 0.5mmol of acidic ionic liquid into 50mL one-necked flasks equipped with stirring bars and reflux condensers. Reflux reaction for 3 hours under vigorous stirring, add ice water to cool, filter, recrystallize the filter residue with 95% ethanol, and dry to obtain pure 9-phenyl-2,3,4,5,6,7-hexahydro-2H-oxa Anthracene-1,8-dione, 92% yield. The acidic ionic liquid catalyst in the filtrate can be recycled after rotary evaporation under reduced pressure to remove water and ethanol, and vacuum drying at 110° C. for 2 h.

Embodiment 2

[0020] Add 10mmol of 4-methoxybenzaldehyde, 20mmol of 1,3-cyclohexanedione, 20mL of absolute ethanol and 0.6mmol of acidic ionic liquid into a 50mL single-necked flask equipped with a stirring bar and a reflux condenser. Reflux for 3.5 hours under vigorous stirring, add ice water to cool, filter, and recrystallize the filter residue with 95% ethanol, dry to obtain pure 9-(4-methoxyphenyl)-2,3,4,5,6,7 - Hexahydro-2H-xanthene-1,8-dione in 95% yield. The acidic ionic liquid catalyst in the filtrate can be recycled after rotary evaporation under reduced pressure to remove water and ethanol, and vacuum drying at 110° C. for 2 h.

Embodiment 3

[0022] Add 10mmol of benzaldehyde, 20mmol of 5,5-dimethyl-1,3-cyclohexanedione, 20mL of absolute ethanol and 0.8mmol of acidic ionic liquid into a 50mL single-necked flask equipped with a stirring bar and a reflux condenser. Under reflux under vigorous stirring for 3 hours, add ice water to cool, filter, recrystallize the filter residue with 95% ethanol, and dry to obtain pure 3,3,6,6-tetramethyl-9-phenyl-2,3,4,5 , 6,7-Hexahydro-2H-xanthene-1,8-dione in 94% yield. The acidic ionic liquid catalyst in the filtrate can be recycled after rotary evaporation to remove water and ethanol, and vacuum drying at 110° C. for 2 h.

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Abstract

The invention provides a method for preparing a xanthene amerantrone derivative via the catalysis of an acidic ionic liquid, and belongs to the technical field of organic chemosynthesis. The method comprises the following steps: performing a condensation reaction, wherein the molar ratio of aromatic aldehyde to a 1,3 hexanedione derivative is 1:2, the molar weight of an acidic ionic liquid catalyst accounts for 5% to 10% of the adopted aromatic aldehyde and the adding amount of absolute ethyl alcohol serving as a reaction solvent accounts for 70% to 90% of the total weight of materials; performing a reflux reaction for 2 to 5 hours under the action of one atmospheric pressure as the reaction pressure; after reacting, cooling by using ice water and filtering; and recrystallizing filter residues by using 95% of ethanol, thereby obtaining the pure xanthene amerantrone derivative. Compared with the traditional preparation method taking acid, alkali and other acidic ionic liquids as the catalysts, the method provided by the invention has the characteristics of being high in catalytic activity and less in catalyst adding amount, realizing catalyst recycling and the like.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for preparing xanthenedione derivatives by catalyzing an acidic ionic liquid. Background technique [0002] Many organic compounds containing pyran rings have important biological and pharmacological activities, such as anti-cancer, anti-dysplasia, anti-hypertension, anti-allergy, etc. The xanthene derivatives contain a pyran ring structure, which is the structural unit of many natural products and is also an important intermediate for the synthesis of other complex organic compounds. The traditional synthesis method of xanthene derivatives is carried out by aldehydes and carbonyl compounds containing active methylene under acid or base catalysis, these acids or bases include p-toluenesulfonic acid, InCl 3 4H 2 O, boric acid or sodium lauryl sulfate, etc. However, the use of the above-mentioned acid and base catalysts often leads to low ...

Claims

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Application Information

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IPC IPC(8): C07D311/82
CPCY02P20/584
Inventor 岳彩波吴胜华
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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