Preparation method of 9,9-dimethyl xanthene

A technology of dimethyl xanthene and diphenyl ether, applied in 9 fields, can solve the problems of low production efficiency, high production equipment requirements, and high equipment requirements

Inactive Publication Date: 2020-10-20
HENAN ACADEMY OF SCI CHEM RES INST CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to overcome the insufficient production capacity caused by high operational risk, high production equipment requirements and low production efficiency in the existing 9,9-dimethylxanthene production process, the purpose o

Method used

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  • Preparation method of 9,9-dimethyl xanthene
  • Preparation method of 9,9-dimethyl xanthene
  • Preparation method of 9,9-dimethyl xanthene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Take a 500ml three-neck flask, add 150ml trifluoromethanesulfonic acid and 78g diphenyl ether in sequence, and slowly add 26g of acetone dropwise after the addition is completed. After the addition, raise the temperature to 120°C and keep it for 2 hours. After cooling down to room temperature, pour it into ice water. Adjust the pH to neutral with 20% sodium hydroxide. A large number of light yellow crystals precipitated after standing overnight, filtered, the filtrate was extracted with 500ml of dichloromethane and dried with anhydrous sodium sulfate, the organic layer was rotary evaporated to obtain 83g of crude product, the crude product was recrystallized with 200ml of dichloromethane / methanol mixed solvent 70.6 g of pure product were obtained. The yield was 75%.

Embodiment 2

[0024] Take a 2L four-neck flask, add 50g of acetone and 154g of diphenyl ether in sequence, fill it with argon for protection after the addition, then slowly add 92ml of concentrated sulfuric acid dropwise, after the dropwise temperature rise to 80°C, and keep it warm for 5h. After the reaction was completed, the temperature was lowered to room temperature, the reactants were poured into ice water, and the pH was adjusted to be neutral with 20% sodium hydroxide in mass percent. After standing overnight, it was extracted with 1 L of dichloromethane and dried with anhydrous sodium sulfate. The organic layer was rotary evaporated to obtain 150 g of crude product, which was recrystallized with 600 ml of dichloromethane / methanol mixed solvent to obtain 128 g of pure product. The yield was 70.7%.

Embodiment 3

[0026] Take a 2L four-neck bottle, add 254g methanesulfonic acid and 150g diphenyl ether in sequence, fill with argon after the addition is complete, then slowly add 50g of acetone dropwise, after the dropwise increase the temperature to 120°C, and keep it warm for 5 hours. After the reaction was completed, the temperature was lowered to room temperature, the reactant was poured into ice water, and the pH was adjusted to be neutral with 30% sodium hydroxide by mass percentage. After standing overnight, it was extracted with 1 L of dichloromethane and dried with anhydrous sodium sulfate. The organic layer was rotary evaporated to obtain 157 g of crude product, which was recrystallized with 600 ml of dichloromethane / methanol mixed solvent to obtain 135 g of pure product. The yield was 74.6%.

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Abstract

The invention relates to a safe and efficient preparation method of an important raw material 9,9-dimethyl xanthene of an industrial catalyst Xantphos, and belongs to the technical field of fine chemical engineering. According to the preparation method, diphenyl ether, acetone and an acid catalyst serve as raw materials, a molar ratio of the raw materials is 1:1:(2-5), 9,9-dimethyl xanthene is prepared through a one-pot method, the yield can reach 70%-75%, and the content is 99% or above. According to the method, acid-catalyzed activated acetone and diphenyl ether are adopted for electrophilicsubstitution reaction to replace extremely dangerous trimethylaluminum and xanthone used in the traditional process for reaction, and the method has the characteristics of cheap and easily availableraw materials, safety in operation, high reaction speed, low requirements on production equipment and the like; and the production difficulty of the product is greatly reduced, and the yield of the 9,9-dimethyl xanthene can be rapidly increased.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to a preparation method of 9,9-dimethylxanthene. Background technique [0002] 9,9-Dimethylxanthene is an important fine chemical intermediate, mainly used in the preparation of industrial phosphorus ligand catalyst 4,5-bis(diphenylphosphine)-9,9-dimethyloxa Anthracene (Xantphos), a derivative of 9,9-dimethylxanthene has excellent hole transport properties, and can also be used in fields such as liquid crystal materials, solar cells, and catalytic materials, especially its downstream product Xantphos with its special The structure is widely used in palladium-catalyzed Suzuki, Negishi, Stille, Heck, etc. coupling reactions. As the demand for Xantphos in the pharmaceutical and optoelectronic material industries increases year by year, it is estimated that the annual demand for this phosphorus ligand in the market will be more than 20 tons in the next few years. [0003] In the ...

Claims

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Application Information

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IPC IPC(8): C07D311/82
CPCC07D311/82
Inventor 郑付伟韩福娇陈海涛李德锦杨柳王文新
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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