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Diphenylmethane compound and preparation method thereof

A technology of diphenylmethane and diphenylmethanol, which is applied in the field of diphenylmethane compounds and their preparation, can solve the problems of dangerous operation process, complicated reaction process, narrow application range and the like, and achieves expansion of use range and simple operation. , the effect of high product purity

Pending Publication Date: 2022-04-08
上海泰坦科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its reaction process is complicated and there are too many side reactions
As for the method of hydroxyl reduction, it is generally referred to the high-temperature reduction of Huang Minglong reaction with hydrazine hydrate, and the operation process is more dangerous.
Catalytic reduction of other metals is difficult to complete the reaction, and the application range is narrow

Method used

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  • Diphenylmethane compound and preparation method thereof
  • Diphenylmethane compound and preparation method thereof
  • Diphenylmethane compound and preparation method thereof

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preparation example Construction

[0036]

[0037] The preparation method of diphenylmethane compound of the present invention comprises the steps:

[0038] (1), iodine (I 2 , 1eq), (1mmol) diphenylmethanol compound and (6mL) acetic acid (AcOH) were stirred evenly under nitrogen protection in a flask equipped with a condenser to obtain the first mixed solution, which was a black solution; then A reducing agent (H 3 PO 2 ) (50% aq., 0.5mL; 5mmol), the color of the solution gradually becomes lighter, and the second mixed solution is obtained, which is finally a yellow-brown solution;

[0039] (2) After dropping, the second mixed solution was heated, and then stirred. At this time, the solution was light yellow and clear, and the reaction was detected by thin layer chromatography (TLC) (TLC: PE / EA=10). Add water to dilute, and the solution becomes cloudy at this time, and it is a white suspension. Extract with 10mL of petroleum ether (PE), wash the aqueous phase with 3mL of PE, and wash the combined organic ...

Embodiment 1

[0056] The preparation method of the 2-methyldiphenylmethane of the present embodiment comprises the steps:

[0057] (1), iodine (7.5g, 30mmol), 2-methyldiphenylcarbinol (5.99g, 30mmol) and acetic acid (190mL) were stirred evenly under nitrogen protection in a flask equipped with a condenser to obtain the first mixture liquid, which is a black solution; wherein, the stirring temperature is 25° C., and the stirring time is 5 minutes. Then, hypophosphorous acid (50% aq., 15 mL; 145 mmol) was added to the first mixed solution, and the color of the solution gradually became lighter to obtain the second mixed solution, which was finally a yellow-brown solution.

[0058] (2) After dropping, the second mixed solution was heated to 60° C. for 2 hours, and then stirred for 2 hours. At this time, the solution was light yellow and clear, and the reaction was detected by TLC. Add 200mL of water to dilute, then the solution becomes cloudy and becomes a white suspension. Extracted with PE...

Embodiment 2

[0064] The preparation method of the 4-methoxydiphenylmethane of the present embodiment comprises the steps:

[0065] (1), iodine (7.5g, 30mmol), 4-methoxydiphenylcarbinol (6.5g, 30mmol) and acetic acid (190mL) were stirred uniformly under nitrogen protection in a flask equipped with a condenser to obtain the first The mixed solution is a black solution; wherein, the stirring temperature is 20° C., and the stirring time is 3 minutes. Then, hypophosphorous acid (50% aq., 15 mL; 145 mmol) was added to the first mixed solution, and the color of the solution gradually became lighter to obtain the second mixed solution, which was finally a yellow-brown solution.

[0066] (2) After dropping, the second mixed solution was heated to 50° C. for 2.5 hours, and then stirred for 1 hour. At this time, the solution was light yellow and clear, and the reaction was detected by TLC. Add 200mL of water to dilute, then the solution becomes cloudy and becomes a white suspension. Extracted with ...

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Abstract

The invention provides a diphenylmethane compound and a preparation method thereof.The preparation method comprises the steps that iodine, a diphenylmethanol compound and acetic acid are stirred under nitrogen protection, then a reducing agent is added, a mixed solution is obtained, and the reducing agent is hypophosphorous acid; the mixed solution is heated and then stirred, thin layer chromatography is used for detecting that the reaction is finished, extraction, washing, drying and concentration are carried out, and functional groups in the diphenyl methanol compound are selected from one or more of chlorine, bromine, methyl, methoxyl or hydrogen; in the prior art, the metal reduction reaction carried out by using hydrazine hydrate often needs high temperature, but the preparation method disclosed by the invention can efficiently and completely react within 8 hours at the temperature of not more than 70 DEG C; according to the method, the diphenylmethane compound can be synthesized from the benzhydrol compound safely, reliably and mildly, no hazardous gas and other hazardous products are generated, impurities are easy to remove, the reaction is clean, the obtained product is high in purity, column chromatography purification is not needed, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a diphenylmethane compound and a preparation method thereof. Background technique [0002] With the enrichment of chemical reagents, it not only promotes the rapid development of medical technology, but also the field of material chemistry is changing with each passing day. Diphenylmethane compounds have gradually been widely used in the field of chemical materials. Tests have shown that diphenylmethane compounds have good chemoselectivity and tolerance to various reactive functional groups, and chemical materials made from them generally have high temperature resistance, corrosion resistance and superior mechanical properties. And it has the advantages of easy to obtain raw materials, high reaction efficiency, low toxicity and convenient synthesis. [0003] The development of new synthetic methods for diphenylmethane compounds is also in continuous optimi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/22C07C15/16C07C41/18C07C43/205C07C17/35C07C25/18
Inventor 谢应波张庆张华罗桂云曹云程德豪
Owner 上海泰坦科技股份有限公司
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