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A kind of electrochemical preparation method of n-(3,5-dimethyl-4-hydroxyphenyl) acetamide

A technology of hydroxyphenyl and dimethylphenol, which is applied in the field of electrochemical organic synthesis, can solve the problems of high energy consumption, and achieve the effects of good reaction selectivity, simple raw materials, and high yield

Inactive Publication Date: 2019-11-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] All of the above synthetic pathways must first obtain aniline compounds before further forming paracetamol compounds. High temperature operation has certain risks and consumes a lot of energy.

Method used

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  • A kind of electrochemical preparation method of n-(3,5-dimethyl-4-hydroxyphenyl) acetamide
  • A kind of electrochemical preparation method of n-(3,5-dimethyl-4-hydroxyphenyl) acetamide
  • A kind of electrochemical preparation method of n-(3,5-dimethyl-4-hydroxyphenyl) acetamide

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Experimental program
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Effect test

Embodiment 1

[0030] With metal platinum wire as anode and platinum sheet as cathode, add 0.5mmol sodium fluoroborate, 0.03mmol nickel chloride, 0.3mmol 2,6-dimethylphenol, 0.15mmol trifluoroacetic acid, 0.075mmol fluorine Potassium chloride, 200uL tert-butanol, 5mL acetonitrile, magnetic stirrer, cover the lid, turn on the power, adjust the current to 5mA, and electrolyze at room temperature for 5h. After the reaction, the reaction liquid was extracted with ethyl acetate, and the corresponding product 3 was obtained after separation and purification, and the yield of the product 3 was 73%. The reaction scheme of the present embodiment is as follows:

[0031]

[0032] The proton nuclear magnetic resonance spectrum figure of present embodiment product is as figure 1 Shown: 1 HNMR (400MHz, DMSO-d 6 ): δ (ppm) 9.50 (s, 1H), 7.92 (s, 1H), 7.10 (s, 2H), 2.12 (s, 6H), 1.97 (s, 3H); figure 2 Shown: 13 CNMR (100MHz, DMSO-d 6 ): δ (ppm) 167.6, 149.0, 131.2, 124.4, 119.7, 23.9, 16.9.

[00...

Embodiment 2

[0035] With metal platinum wire as anode and platinum sheet as cathode, add 1mmol sodium fluoroborate, 0.06mmol nickel chloride, 0.3mmol 2,6-dimethylphenol, 0.18mmol trifluoroacetic acid, 0.0825mmol fluoride Potassium, 200uL tert-butanol, 5mL acetonitrile, magnetic stirrer, cover the lid, turn on the power, adjust the current to 3mA, and electrolyze at room temperature for 8h. After the reaction, the reaction liquid was extracted with ethyl acetate, and the corresponding product 3 was obtained after separation and purification, and the yield of the product 3 was 60%.

Embodiment 3

[0037] With metal platinum wire as anode and platinum sheet as cathode, add 0.75mmol sodium fluoroborate, 0.045mmol nickel chloride, 0.3mmol 2,6-dimethylphenol, 0.21mmol trifluoroacetic acid, 0.09mmol fluorine Potassium chloride, 200uL tert-butanol, 5mL acetonitrile, magnetic stirrer, cover the lid, turn on the power, adjust the current to 4mA, and electrolyze at room temperature for 6.5h. After the reaction, the reaction liquid was extracted with ethyl acetate, and the corresponding product 3 was obtained after separation and purification, and the yield of the product 3 was 65%.

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Abstract

The invention discloses an electrochemical preparation method of N-(3,5-dimethyl-4-hydroxyphenyl)acetamide, and belongs to the technical field of electrochemical organic synthesis. The preparation method comprises the following steps: adding acetonitrile and corresponding electrolyte, 2,6-dimethylphenol, nickel chloride, trifluoroacetic acid, potassium fluoride and tert-butanol to a separator-freeelectrolytic tank sequentially, inserting an anode and a cathode, performing stirring and electrification, performing reaction under the condition of constant current, performing organic extraction on an electrolyte with an organic solvent after the reaction, and then performing separation and purification to obtain N-(3,5-dimethyl-4-hydroxyphenyl)acetamide. The electrodes are general inert electrodes and need not to be modified, yield is higher, selectivity is good, and the reaction system is simple, effective and environmentally friendly; the reaction in the method is operated at normal temperature under normal pressure, and is simple and safe.

Description

technical field [0001] The invention belongs to the technical field of electrochemical organic synthesis, and in particular relates to an electrochemical preparation method of N-(3,5-dimethyl-4-hydroxyphenyl)acetamide. Background technique [0002] N-(3,5-Dimethyl-4-hydroxyphenyl)acetamide is an important paracetamol derivative. Paracetamol is the most commonly used non-anti-inflammatory antipyretic analgesic, with weak analgesic effect and no anti-inflammatory and anti-rheumatic effect. Some 3,5-disubstituted paracetamol derivatives have attracted the research interest of chemists due to their advantages in pharmacology and antioxidant properties. [0003] The preparation method of paracetamol is mainly obtained by acidifying p-aminophenol at high temperature and reacting with acid anhydride or acid chloride, which has large production limitations. In 2011, Gu et al [M.Li; L.Hu; X.Cao; H.Hong; J.Lu; H.Gu.Chem.Eur.J.2011,17,2763-2768.] reported a new The method for synthe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 黄精美简文倩
Owner SOUTH CHINA UNIV OF TECH
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