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Method for catalytically dehydrogenating and oxidizing aryl secondary alcohol into ketone

A technology for catalytic dehydrogenation and aryl secondary alcohols, applied in chemical instruments and methods, dehydrogenation preparation, carbon-based compound preparation, etc., can solve problems such as slow disappearance or decomposition, pollution of the environment by useless by-products, instability, etc., to achieve Ease of handling, great application potential, and mild reaction conditions

Active Publication Date: 2019-11-22
XI'AN PETROLEUM UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the waste of a large amount of stoichiometric reagents and the useless by-products generated by most non-metallic oxidants seriously pollute the environment, and the catalysts used are usually in the form of expensive cobalt, copper, and iron complexes, which are usually not available. Stable, will slowly disappear or decompose under oxidizing conditions

Method used

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  • Method for catalytically dehydrogenating and oxidizing aryl secondary alcohol into ketone
  • Method for catalytically dehydrogenating and oxidizing aryl secondary alcohol into ketone
  • Method for catalytically dehydrogenating and oxidizing aryl secondary alcohol into ketone

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Taking the preparation of the following formula compound benzophenone as an example, the raw materials used and the preparation method thereof are as follows:

[0027]

[0028] In the reaction tube, add p-toluenesulfonic acid (0.3mmol, 0.50g), tert-butyl chloride (0.6mmol, 0.030mL), benzhydryl alcohol (0.6mmol, 0.11g) in dichloroethane (0.5mL) , stir well at room temperature, then stir and heat up to 60°C, stop the reaction after 2 hours of reaction, add 2mL saturated aqueous sodium bicarbonate solution to the system, extract three times with 10mL ethyl acetate, combine the organic phases, and dry with anhydrous sodium sulfate , filtered, concentrated, and separated by column chromatography (hexane / EtOAc) to obtain a white solid product with an isolated yield of 83%. The resulting product was characterized by a Bruker Avance superconducting Fourier digital NMR spectrometer, and the characterization data are as follows: 1 H NMR (600MHz, CDCl 3 )δ7.56(dd, J=8.4,1.2Hz...

Embodiment 2

[0030] Taking the preparation of the following formula compound 4-methylbenzophenone as an example, the raw materials used and the preparation method thereof are as follows:

[0031]

Embodiment 3

[0033] Example 3

[0034] Taking the preparation of the following formula compound 4-nitrobenzophenone as an example, the raw materials used and the preparation method thereof are as follows:

[0035]

[0036] In embodiment 3, the diphenyl alcohol used is replaced with equimolar 4-nitrobenzophenone, and other steps are identical with embodiment 1, is prepared into white solid 4-nitrobenzophenone, and its isolated yield is 72%, the characterization data is: 1 H NMR (600MHz, CDCl 3 )δ8.26(d, J=8.2Hz, 2H), 7.92(d, J=8.1Hz, 2H), 7.82–7.77(m, 2H), 7.57(d, J=7.3Hz, 1H), 7.47( t,J=7.7Hz,2H); 13 C NMR (151MHz, CDCl 3 )δ194.8, 149.1, 142.9, 136.3, 133.5, 130.7, 130.2, 128.7, 123.6

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Abstract

The invention discloses a method for catalytically dehydrogenating and oxidizing aryl secondary alcohol into ketone. The method comprises the following steps: dissolving the aryl secondary alcohol inan organic solvent, and reacting at 40-120 DEG C in the presence of an acid catalyst and a cocatalyst to obtain substituted aryl ketone, wherein the acid is aryl sulfonic acid (ArSO3H), alkyl sulfonicacid (RSO3H) or boron trifluoride diethyl ether, and the cocatalyst is tertiary halogenated hydrocarbon or benzyl halogenated hydrocarbon. According to the method, a metal catalyst and an oxidizing agent are not used, the adopted catalyst is cheap and non-toxic and can tolerate water and air, the reaction condition is mild, and the method is simple to operate and high in atom economy, and can beused for large scale production.

Description

technical field [0001] The invention relates to the conversion reaction of secondary alcohols, in particular to a method for catalytic dehydrogenation and oxidation of aryl secondary alcohols into ketones. Background technique [0002] The selective oxidation of secondary aryl alcohols to ketones is a very important and fundamental class of organic transformations. Its products play a very important role in organic synthesis intermediates, pharmaceutical synthesis, pesticides, spices, and pigments. For example, benzophenone is usually used to synthesize drugs such as diphenhydramine hydrochloride, benztropine hydrobromide and dicyclohexidine, and benzophenone is a fixative. [0003] Stoichiometric chromium(VI), manganese oxidizer, Jones reagent, PDC oxidation system, NaClO solution have been used to complete the oxidation of secondary alcohols (S.V.Ley, A.Madin, in: B.M.Trost, I.Fleming (Eds.) , Comprehensive Organic Synthesis, vol.7, 1991 (pp.305–327); G. Cainelli, G. Car...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C45/29C07C49/786C07C49/813C07C205/45C07C201/12C07D311/86
CPCC07C45/002C07C45/29C07C201/12C07D311/86C07C49/786C07C49/813C07C205/45
Inventor 吴亚李浩韩薇薇陈刚姬悦林智伟
Owner XI'AN PETROLEUM UNIVERSITY
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