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Method for synthesizing acetophenone or benzoic acid compound by oxidizing toluene compound

A technology for benzoic acid and oxidation synthesis, which is applied in the field of synthesizing acetophenone or benzoic acid compounds, can solve the problems of low single conversion rate and limited functional group tolerance, and achieve low cost, mild reaction conditions, and substrate The effect of readily available sources

Active Publication Date: 2021-05-11
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the above-mentioned methods usually require expensive metal catalysts such as cobalt and manganese to realize the oxidation of aromatic hydrocarbons under high temperature and high pressure conditions, and the single conversion rate of the reaction is low, requiring multiple cycles of oxidation reactions, and the functional group tolerance of the reaction is limited.

Method used

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  • Method for synthesizing acetophenone or benzoic acid compound by oxidizing toluene compound
  • Method for synthesizing acetophenone or benzoic acid compound by oxidizing toluene compound
  • Method for synthesizing acetophenone or benzoic acid compound by oxidizing toluene compound

Examples

Experimental program
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Effect test

Embodiment 1

[0020] A method for synthesizing benzoic acid by oxidation of toluene, the steps are as follows:

[0021] In a 25mL quartz tube, add toluene 9.2mg, cerium acetate 3.0mg, ethanol 4.0mg, CH 3 CN 2mL. The resulting mixture was irradiated for 12 hours at 80° C. under a 450 nm light source. Remove CH under reduced pressure 3 CN, column chromatography obtained 11.9 mg of the target product, benzoic acid, with a yield of 98%.

[0022] The product structure is

[0023]

[0024] The NMR data of the product are: 1 H NMR (400MHz, DMSO) δ12.98(s, 1H), 7.95(d, J=8.0Hz, 2H), 7.63(t, J=7.2Hz, 1H), 7.50(t, J=7.6Hz, 2H ). 13 C NMR (100 MHz, DMSO) δ 167.4, 132.9, 130.8, 129.3, 128.6.

Embodiment 2

[0026] A method for synthesizing benzoic acid by oxidation of toluene, the steps are as follows:

[0027] In a 25mL quartz tube, add toluene 9.2mg, cerium acetate 3.0mg, ethanol 4.0mg, CH 3 CN 2mL. The resulting mixture was irradiated for 12 hours at 60° C. under a 450 nm light source. Remove CH under reduced pressure 3 CN, column chromatography obtained 10.9 mg of the target product, benzoic acid, with a yield of 90%.

[0028] Product structure and NMR data are the same as in Example 1.

[0029] Compared with Example 1, the difference of this example is that the reaction temperature is 60°C.

Embodiment 3

[0031] A method for synthesizing benzoic acid by oxidation of toluene, the steps are as follows:

[0032] In a 25mL quartz tube, add toluene 9.2mg, cerium acetate 3.0mg, ethanol 4.0mg, CH 3 CN 2mL. The resulting mixture was irradiated for 12 hours at 80°C under a 400nm light source. Remove CH under reduced pressure 3 CN, column chromatography obtained 11.2 mg of the target product, benzoic acid, with a yield of 92%.

[0033] Product structure and NMR data are the same as in Example 1.

[0034] Compared with Embodiment 1, the difference of this embodiment is that a 400nm light source is used.

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Abstract

The invention provides a method for synthesizing an acetophenone or benzoic acid compound through oxidation of a toluene compound, and belongs to the field of organic synthesis. The method for synthesizing the acetophenone or benzoic acid compound through oxidation of the toluene compound comprises the following step of: under the action of a reaction catalyst and an initiator, illuminating the toluene compound in an oxygen-containing atmosphere in a solvent to obtain the acetophenone compound or the benzoic acid compound, wherein the reaction catalyst is lanthanide series rare earth metal salt, and the initiator is a C1-C6 alcohol compound. The method has the advantages of abundant and easily available substrate sources, mild reaction conditions, good compatibility of substrate functional groups, simple operation, high reaction safety, low cost and the like.

Description

technical field [0001] The invention relates to a method for synthesizing acetophenone or benzoic acid compounds, in particular to a method for synthesizing acetophenone or benzoic acid compounds by oxidation of toluene compounds, belonging to the field of organic synthesis. Background technique [0002] The direct functionalization of arenes provides a simple route to synthesize high value-added products from cheap raw materials, and the oxidation of arenes has attracted extensive attention of chemists in recent years. [0003] Acetophenone and benzoic acid compounds are widely used in food, medicine, dyes and other chemical industries, and are also an important class of organic synthesis intermediates. At present, there have been a large number of literatures reporting the synthesis methods of acetophenone and benzoic acid, including: benzonitrile hydrolysis method, toluene chlorination hydrolysis method, phthalic anhydride hydrolysis method, alcohol oxidation method, etc....

Claims

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Application Information

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IPC IPC(8): C07C45/36C07C49/786C07C51/265C07C65/21C07C63/06C07C63/331
CPCC07C45/36C07C51/265C07C49/786C07C65/21C07C63/06C07C63/331
Inventor 施章杰王长城房华毅刘烽
Owner FUDAN UNIV
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