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Method for catalytic preparation of triarylmethane compounds by using [EG]2[ZnCl2]

A technology for triaryl methane and aryl methane, which is applied in the field of catalytic preparation of triaryl methane compounds, can solve the problems of corrosive gas generation, inability to recycle, complex post-treatment, etc., achieve mild reaction conditions, simple production, and post-processing simple effect

Inactive Publication Date: 2016-01-13
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of catalyst has some unavoidable disadvantages, such as being unable to recycle, requiring the use of volatile organic solvents, complicated post-treatment, producing corrosive gases and a large amount of waste liquid during the process, and causing serious pollution to the environment, etc.

Method used

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  • Method for catalytic preparation of triarylmethane compounds by using [EG]2[ZnCl2]
  • Method for catalytic preparation of triarylmethane compounds by using [EG]2[ZnCl2]
  • Method for catalytic preparation of triarylmethane compounds by using [EG]2[ZnCl2]

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Experimental method: Take a 25mL round-bottomed flask, add 336mg (2.0mmol) 1,2,4-trimethoxybenzene and 368mg (2.0mmol) benzhydryl alcohol in sequence, stir magnetically, stir at an oil bath temperature of 90°C, and use a thin The progress of the reaction was monitored by layer chromatography. No product was found to form, ie the reaction did not proceed in the absence of DES.

[0017] Reaction equation:

[0018]

Embodiment 2

[0020] Experimental method: take a 25mL round bottom flask, add 336mg (2.0mmol) 1,2,4-trimethoxybenzene and 368mg (2.0mmol) benzhydryl alcohol in sequence, then add 1.04g (4.0mmol) [EG] 2 [ZnCl 2 ], magnetic stirring, stirring at an oil bath temperature of 90°C, monitoring the progress of the reaction by thin-layer chromatography, and stopping the reaction after 1 hour. Based on 1 mole of electron-rich aromatic compounds as the standard, DES([EG] 2 [ZnCl 2 ]) is used in an amount of 2 moles, the amount of diaryl carbinol is 1 mole, the reaction temperature is 90° C., and the reaction time is 1 h.

[0021] Post-treatment, after cooling to room temperature, add 10mL distilled water and 10mL ethyl acetate for extraction, [EG] 2 [ZnCl 2 ] was dissolved in the water phase, the product was dissolved in the ethyl acetate layer, separated, the ethyl acetate layer was washed once with saturated brine, dried over anhydrous magnesium sulfate, and the ethyl acetate was removed by dist...

Embodiment 3

[0025] Experimental method: the water in the water phase in Example 2 was evaporated to dryness, and the obtained catalyst was vacuum-dried and recycled for use. The recovered [EG] 2 [ZnCl 2 ] Repeat the steps of Example 2. This was repeated 4 times, and the yields of the obtained products were 84%, 81%, 78%, and 73%, respectively.

[0026] Reaction equation:

[0027]

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Abstract

The invention relates to a method for catalytic preparation of triarylmethane compounds by using [EG]2[ZnCl2], especially to a method for catalytic preparation of the triarylmethane compounds by using a deep eutectic solvent [EG]2[ZnCl2] through Friedel-Crafts alkylation. Electron-rich aromatic hydrocarbons and diarylcarbinols are used as substrates, [EG]2[ZnCl2] is used as both the reaction solvent and catalyst, and Friedel-Crafts alkylation is carried out to prepare the triarylmethane compounds. According to the invention, [EG]2[ZnCl2] used in the method has high catalytic activity, high selectivity and high reaction yield, can effectively reduce the usage amounts of other organic solvents and toxic catalysts and alleviates corrosivity of the catalyst to equipment, and post-treatment is simple and convenient.

Description

technical field [0001] The invention relates to a method for catalyzing the preparation of triarylmethane compounds, more specifically, to a method for catalyzing the formation of p-triarylmethane compounds through Friedel-Crafts alkylation reaction using a deep eutectic solvent. Background technique [0002] Triarylmethanes are important intermediates in medicine, fuel and materials chemistry. For example, basic fuchsin is a triarylmethane compound that can be used to stain substances such as collagen fibers. Cetirizine, a triaryl methane compound, is a class of useful antiallergic drugs and the like. In addition, some triarylmethane compounds also have certain biological activities, and have important applications in antiviral and antitumor aspects. [0003] Since triaryl methane compounds have multiple uses, there are many reports on their synthesis methods. At present, the main synthesis methods are: Friedel-Crafts alkylation reaction, coupling reaction, reduction rea...

Claims

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Application Information

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IPC IPC(8): C07C41/30C07C43/205C07C43/23C07C43/225
CPCC07C41/30C07C43/205C07C43/23C07C43/225
Inventor 王爱玲邢鹏飞郑学仿
Owner DALIAN UNIV