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A kind of convenient preparation method of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol and its derivatives

A technology of diphenol and resorcinol, which is applied in the field of organic compound preparation, can solve the problems of long-term yield, long reaction process, and long reaction time, and achieve the effects of shortening reaction time, improving efficiency, and saving energy

Active Publication Date: 2020-10-16
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Abstract
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  • Claims
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Problems solved by technology

[0003] At present, the preparation method of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol and its derivatives is reported in the early literature, which takes a long time and the yield is low
In 2011, Fu Guiyun et al. (Applied Chemistry, 2011, 28(8): 974-976) heated xanthone and thionyl chloride under reflux for 12 hours to prepare the intermediate 9,9-dichloroxanthene, and then The intermediate 9,9-dichloroxanthene and methyl-substituted phenol were refluxed for 8 hours, and toluene was recrystallized to generate a bisphenol compound containing a xanthene structure with a yield of 81%. Product, long reaction process, long time, high temperature
In 2015, Zhou Y et al. (ARKIVOC, 2015,99:109.) in MeSO 3 Under the catalysis of H, spiro[fluorene-9,9'-xanthene]-3',6'-diphenol was prepared by reacting 9-fluorenone with resorcinol, and the reaction was 6-8 hours at a temperature of about 110°C , the yield is about 78%, and the reaction time is longer

Method used

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  • A kind of convenient preparation method of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol and its derivatives
  • A kind of convenient preparation method of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol and its derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Put 20mL of toluene, 3.6g (0.02mol) of 9-fluorenone, and 8.8g (0.08mol) of resorcinol into the reaction flask in turn, and add 0.172g (0.001mol) of p-toluenesulfonic acid under stirring condition; put the reaction flask Put into the microwave reactor that air condensing tube and reflux condensing device are housed, adjust microwave power to 600W, microwave reaction 20min (experiment verification, this reaction puts reaction bottle into the common reactor that air condensing tube and reflux condensing device are housed (that is, without microwave conditions), heated to a reaction temperature of 120°C, reacted for 12h, and the yield was only 65%); cooled to room temperature, added an appropriate amount of water, stirred for 20 minutes, solids were precipitated, and filtered; the filter cake obtained from the above reaction was used Dissolve in methanol, filter out the insolubles to obtain a clear and transparent filtrate, precipitate under reduced pressure, recrystallize t...

Embodiment 2

[0028] Put 20 mL of toluene, 3.6 g (0.02 mol) of 9-fluorenone, and 11 g (0.1 mol) of resorcinol into the reaction flask in turn, and add SO 4 2- / TiO 2 0.2g; put the reaction bottle into a microwave reactor equipped with an air condenser and a reflux condensing device, adjust the microwave power to 600W, and microwave for 25min; filter out the solid acid SO while it is hot 4 2- / TiO 2 (The solid acid can be recycled and reused), cooled to room temperature, added an appropriate amount of water, stirred for 30 minutes, and the solid was separated out, filtered; the filter cake obtained by the above reaction was dissolved with an ethanol solvent, and the insolubles were filtered to obtain a clear and transparent filtrate. Pressure precipitation and recrystallization of the crude product gave 6.0 g of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol with a yield of 83%. The melting point and NMR spectrum were the same as in Example 1.

Embodiment 3

[0030] Put 20mL of toluene, 3.6g (0.02mol) of 9-fluorenone, and 4.4g (0.04mol) of resorcinol into the reaction flask in turn, and add 0.192g (0.002mol) of methanesulfonic acid under stirring condition; Put it into a microwave reactor equipped with an air condenser and a reflux condensing device, adjust the microwave power to 800W, and react with the microwave for 10 minutes; cool to room temperature, add an appropriate amount of water, stir for 40 minutes, the solid is precipitated, and filtered; the filter cake obtained from the above reaction Dissolved with ether solvent, filtered the insoluble matter to obtain a clear and transparent filtrate, desolvated under reduced pressure, recrystallized the crude product to obtain 6.0 g of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol, Yield is 53%; Melting point and nuclear magnetic resonance spectrum are the same as embodiment 1.

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Abstract

The invention belongs to the technical field of organic compound preparation, and relates to a preparation method of spiral shell [fluorenes-9, 9'-xanthene]-3', 6'-diphenol and derivatives of the spiral shell [fluorenes-9, 9'-xanthene]-3', 6'-diphenol. The preparation method comprises the steps that an organic solvent, 9-fluorenone and resorcinol are sequentially added, then a catalyst is added, the mixture is placed in a microwave reactor with an air condensing tube and a reflux condensing device and reacted for 5-40 minutes under a stirring condition, an appropriate amount of water is addedafter cooling, stirring is performed for 20-40 minutes, a solid is precipitated by filtration, the obtained solid is dissolved by using an alcohol solvent or an ether solvent, and filtration and crystallization are performed to obtain a final product with a yield of more than 80%. The preparation method has the beneficial effects that the reaction time is greatly shortened, the reaction yield is improved, the cost is saved, and the preparation method is environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and in particular relates to a preparation method of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol and derivatives thereof. Background technique [0002] Polyfluorene derivatives, organic electronic device materials, have the characteristics of high refractive index, good solubility and high film-forming properties, and have been widely used. In recent years, spiro compounds have become the development direction of organic electronic device materials due to their stable optical properties. Spiro[fluorene-9,9'-xanthene]-3',6'-diphenol and its derivatives are important monomers of spiro-ring electronic materials. [0003] At present, the preparation method of spiro[fluorene-9,9'-xanthene]-3',6'-diphenol and its derivatives reported in the early literatures takes a long time and the yield is low. In 2011, Fu Guiyun et al. (Applied Chemistry, 2011, 28(8): 974-976) heated xanthon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/96
CPCC07D311/96
Inventor 肖尖陆国元陈强
Owner CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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