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Synthetic method of diaryl methanol compound

The technology of a diaryl methanol and a synthesis method is applied in the environmental friendly technical field, can solve the problems of low yield, high toxicity of aryl formaldehyde, etc., and achieves the effects of easy separation and purification, safe and stable raw materials, and mild synthesis conditions

Active Publication Date: 2016-07-27
YICHUN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The reaction raw material aryl formaldehyde in this method is highly toxic, and by-products are generated in the reaction, and the yield is not high

Method used

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  • Synthetic method of diaryl methanol compound
  • Synthetic method of diaryl methanol compound
  • Synthetic method of diaryl methanol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of diphenylcarbinol

[0042]

[0043] Add 1mmol of benzyl bromide, 1.2mmol of phenylboronic acid, 2mmol of anhydrous potassium carbonate, 2.5mmol of PEG2000, 0.01mmol of catalyst, 5ml of pure water into the reaction flask, and react for 4 hours in the air at room temperature, stop the reaction, and divide with about 40ml of ethyl acetate. Extract three times to obtain the organic phase of ethyl acetate, add 2-3 tablespoons of anhydrous sodium sulfate and let stand for 4 hours to remove water, filter and rotary evaporate, use TLC method to separate, use (n-hexane:dichloromethane=7:1, v : v) The product was isolated as a developer, and recrystallized with ethanol to obtain diphenylmethanol with a yield of 80%.

Embodiment 2

[0044] Embodiment 2: the preparation of two (4-fluorophenyl) methanol

[0045]

[0046] Add 1mmol of 4-fluorobenzyl bromide, 1.2mmol of 4-fluorophenylboronic acid, 2mmol of anhydrous potassium carbonate, 2.5mmol of PEG2000, 0.01mmol of catalyst, 5ml of pure water into the reaction flask, and react for 4h at room temperature in air, stop the reaction, and use About 40ml of ethyl acetate was extracted three times to obtain the organic phase of ethyl acetate, add 2-3 spoons of anhydrous sodium sulfate and let it stand for 4h to remove water, filter and rotary evaporate, use TLC method to separate, use (n-hexane: dichloromethane =7:1, v:v) The product was isolated as a developer and recrystallized with ethanol to obtain bis(4-fluorophenyl)methanol with a yield of 75%.

Embodiment 3

[0047] Embodiment 3: the preparation of p-methylbenzhydryl alcohol

[0048]

[0049] Add 1mmol of 4-methylbenzyl bromide, 1.2mmol of phenylboronic acid, 2mmol of anhydrous potassium carbonate, 2.5mmol of PEG2000, 0.01mmol of catalyst, and 5ml of pure water into the reaction flask, and react for 4 hours in the air at room temperature, stop the reaction, and use about 40ml Ethyl acetate was extracted three times to obtain the organic phase of ethyl acetate. Add 2-3 spoons of anhydrous sodium sulfate and let it stand for 4 hours to remove water. Suction filtration and rotary steaming were used for separation by TLC. : 1, v: v) The product was isolated as a developer, and recrystallized with ethanol to obtain p-methylbenzhydryl alcohol with a yield of 85%.

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PUM

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Abstract

The invention discloses a synthetic method of a diaryl methanol compound. Compared with a reported method for obtaining the diaryl methanol compound through catalytic reduction by taking diaryl ketone as an initial raw material, the method is characterized by taking substituted benzyl bromide and substituted phenylboronic acid which are cheap and easy to obtain as initial raw materials, reacting for 4 hours in an alkaline solution, water or a mixed solvent of the water and an organic solvent under room temperature in air, and carrying out simple separation and purification operation, thus obtaining a pure product. A catalyst adopted in the method is a palladium compound / an in-situ catalytic system prepared from phosphorus- and oxygen-containing carboxylic acids ligands, the catalytic system is cheap in price, high in catalytic activity and good in selectivity and is stable in the air and a water solution, the diaryl methanol compound is compounded through a method of catalyzing the substituted benzyl bromide and the substituted phenylboronic acid and a 'one-pot reaction method' of hydrogen peroxide, the reaction steps are less, after-treatment is simple, the product is easy to separate and purify, the yield is high, and the mixed solvent is prepared from cheap and easy-to-obtain water and the organic solvent, so that the environment is not polluted, and environment protection is realized.

Description

technical field [0001] The invention relates to the synthesis field of fine chemical industry and medicinal chemistry, and relates to the important intermediates of synthesizing antiallergic drugs modafinil, atrafenil and cetirizine hydrochloride, etc. An environmentally friendly technique for the one-pot synthesis of methanol-based compounds. Background technique [0002] Diaryl carbinol compounds are important intermediates for the synthesis of antiallergic drugs such as modafinil, atrafenil and cetirizine hydrochloride. The synthesis methods reported in the literature include metal reduction method, catalytic hydrogenation reduction method, metal hydride reduction method and Suzuki coupling method, etc. [0003] [0004] 1. Metal reduction method (aluminum, magnesium, zinc and other metals are reduced by acid or alkali as an initiator) [0005] [0006] 2. Catalytic hydrogenation reduction method [0007] [0008] 3. Metal hydride reduction method [0009] ...

Claims

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Application Information

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IPC IPC(8): C07C29/36C07C33/24C07C33/46B01J31/24
CPCB01J31/2409B01J2531/0241B01J2531/824C07C29/36C07C33/24C07C33/46
Inventor 郭孟萍王武
Owner YICHUN UNIVERSITY
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