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Electrochemical synthesis method of 2-aryl-1, 2-diacetophenone

A technology of benzophenone and synthesis method, which is applied in the direction of electrolytic components, electrolytic process, electrolytic organic production, etc., can solve the problems of large pollution, high energy consumption, complex ligand metal catalysts, etc., and achieve mild reaction conditions and cheap raw materials Easy to obtain and low production cost

Active Publication Date: 2021-12-21
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although multiple methods for synthesizing aryl ketones have been disclosed in the prior art, these methods all belong to traditional chemical synthesis methods, which inevitably have large pollution and consumption Can you wait for more questions:
[0004]1) Use a cleaning oxidizing agent such as TBHP (tert-butyl alcohol peroxide) or H2O2( hydrogen peroxide), however these methods often require complex ligands and highly loaded metal catalysts;
[0005]2) The chemical oxidant used will require higher cost and produce a lot of solid waste;
[0006] Therefore, the existing synthetic methods still cannot meet the large-scale and simple requirements for the synthetic methods of aryl congeners

Method used

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  • Electrochemical synthesis method of 2-aryl-1, 2-diacetophenone
  • Electrochemical synthesis method of 2-aryl-1, 2-diacetophenone
  • Electrochemical synthesis method of 2-aryl-1, 2-diacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The reaction equation is:

[0041]

[0042] Wash and dry a 10ml chicken mouth bottle, prepare a platinum wire and a silver wire to pass through the rubber stopper of a bottle as a wire, and connect two pieces of graphite felt (2cm×1cm×0.5cm) to the lower end of the wire , use Teflon film to separate the two pieces of graphite felt, and then use Teflon thread to fasten the two pieces of graphite felt. The graphite felt connected with platinum wire is used as the anode of the electrolysis reaction, and the graphite felt connected with the silver wire is used as the cathode of the electrolysis reaction. Add 0.2mmol triarylethylene (compound of formula 1a) and 0.1mmolLiClO 4 , the reaction bottle was filled with oxygen 3 times, and then 5 mL of dry CH was added 3 CN. The reaction was carried out at a constant voltage of 5V at room temperature, and the reaction was completed after 1.5h. After the reaction, the solvent was removed under reduced pressure, and then separ...

Embodiment 2

[0047] The reaction equation is:

[0048]

[0049] Using the compound of formula 1b as the raw material, other operations were the same as in Example 1 to obtain 49 mg of the compound of formula 2b with a yield of 84%. The nuclear magnetic data of gained formula 2b compound is:

[0050] 1 H NMR (400MHz, Chloroform-d) δ=8.08–8.00(m,2H),7.58–7.52(m,1H),7.49–7.42(m,2H),7.39–7.34(m,2H),7.33–7.25 (m,5H),7.09–7.00(m,2H),6.06(s,1H).

[0051] 13 C NMR (100MHz, Chloroform-d) δ=198.03, 161.93 (d, J=245.9Hz), 138.9, 136.66, 134.90 (d, J=3.3Hz), 133.12, 130.70 (d, J=8.0Hz), 128.96 ,128.90,128.85,128.63,127.27,115.49(d,J=21.4Hz),58.51.

[0052] 19 F NMR (376 MHz, Chloroform-d) δ = -115.59.

Embodiment 3

[0054] The reaction equation is:

[0055]

[0056] Using the compound of formula 1c as the raw material, other operations were the same as in Example 1 to obtain 50 mg of the compound of formula 2c with a yield of 82%. The nuclear magnetic data of gained formula 2c compound is:

[0057] 1 H NMR (400MHz, Chloroform-d) δ=8.00–7.98(m,2H),7.55–7.51(m,1H),7.45–7.39(m,2H),7.36–7.25(m,7H),7.23–7.18 (m,2H),6.01(s,1H).

[0058] 13 C NMR (100 MHz, Chloroform-d) δ = 197.79, 138.61, 137.68, 136.60, 133.19, 133.11, 130.50, 128.98, 128.92, 128.90, 128.79, 128.67, 127.36, 58.68.

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Abstract

The invention discloses an electrochemical synthesis method of 2-aryl-1, 2-diacetophenone, and the method comprises the following steps: by taking triaryl ethylene as a raw material, LiClO4 as an electrolyte and CH3CN as a solvent, carrying out constant-voltage reaction in an oxygen atmosphere at normal temperature through an electrode, after the reaction is finished, reducing pressure to remove the solvent, and carrying out column chromatography separation to obtain the product 2-aryl-1, 2-diacetophenone, namely the 2-aryl-1, 2-diacetophenone. The 2-aryl-1, 2-diacetophenone is prepared by adopting an electrochemical synthesis method, the reaction condition is mild, the reaction is room temperature, the reaction pressure is nearly normal pressure, the post-treatment is simple, the raw materials are cheap and easy to obtain, the production cost is low, the reaction steps are few, and only one-step reaction is adopted. The reaction is green and environment-friendly, current and oxygen participate in oxidation in the reaction process, and transition metal and a strong oxidant do not need to be used.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the synthesis of aryl ketones, in particular to an electrochemical synthesis method of 2-aryl-1,2-benzophenone. Background technique [0002] Aryl ketones are an important class of organic compounds, which widely exist in a variety of physiologically active natural products, and can be used to synthesize a variety of final products such as pharmaceutical compounds through the reaction of carbonyl groups, so they are widely used in medicine, Food, materials and other fields are playing an increasingly important role. It is precisely because of such a wide range of uses and chemical properties of aryl ketones that people have conducted a lot of research on their synthesis methods and achieved many results. [0003] Although various methods for synthesizing aryl ketones are disclosed in the prior art, these methods all belong to traditional chemical synthesis methods, which...

Claims

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Application Information

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IPC IPC(8): C25B3/07C25B3/11C25B3/20C25B3/23
CPCC25B3/07C25B3/11C25B3/20C25B3/23
Inventor 李进王健洪坤端木传嵩徐海青
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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