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Electrooxidative Preparation Method of Kresstrobin and Trifloxystrobin Intermediates

A technology of electro-oxidation and electrolytic cell, which is applied in the direction of oxime preparation, electrolytic components, electrolytic process, etc., can solve the problems of complex reaction process and harsh conditions, and achieve the effect of simplifying the process and reducing production costs

Active Publication Date: 2022-04-08
湖北中迅长青科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction process of this route is complicated and the conditions are harsh

Method used

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  • Electrooxidative Preparation Method of Kresstrobin and Trifloxystrobin Intermediates
  • Electrooxidative Preparation Method of Kresstrobin and Trifloxystrobin Intermediates
  • Electrooxidative Preparation Method of Kresstrobin and Trifloxystrobin Intermediates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Electrooxidative Preparation of Methyl 2-Methylacetophenone

[0051]

[0052] Install the anode in the electrolyzer (carbon felt: 10×10×2mm 3 ) and cathode (platinum mesh: 10×10×2mm 3 ); Add a magnetic stir bar in the electrolytic cell, 82mg (0.5mmol) methyl 2-methylphenylacetate, 163mg (1.0mmol) N-hydroxyphthalimide and 342mg (1mmol) tetrabutyl Add 10 mL of acetonitrile and 2 mL of water to dissolve ammonium chlorate, add 80 mg (1 mmol) of pyridine, electrolyze with a constant current of 10 mA at 20 °C for 8 h, spin evaporate the reaction solution, dissolve in ethyl acetate, wash with water three times, and dry the organic layer with anhydrous sodium sulfate , rotary steamed to obtain 76mg methyl 2-methylacetophenone; yield 85%; 1 HNMR (400MHz, CDCl 3 )δ: 7.71~7.28 (m, 4H, benzene ring), 3.96 (s, 3H, OCH 3 ), 2.61 (s, 3H, CH 3 ).

Embodiment 2

[0054] Electrooxidative Preparation of Ethyl 2-Methylacetophenone

[0055]

[0056] Install the anode in the electrolyzer (carbon felt: 10×10×2mm 3 ) and cathode (platinum mesh: 10×10×2mm 3); Add a magnetic stirrer in the electrolytic cell, 89mg (0.5mmol) ethyl 2-methylphenylacetate, 82mg (0.5mmol) N-hydroxyphthalimide and 342mg (1mmol) tetrabutyl Add 10 mL of acetonitrile and 2 mL of water to dissolve ammonium perchlorate, add 80 mg (1 mmol) of pyridine, electrolyze with a constant current of 10 mA at 50 ° C for 3 h, spin the reaction solution, dissolve in ethyl acetate, wash with water three times, and dry the organic layer with anhydrous sodium sulfate , rotary steamed to obtain 84mg methyl 2-methylacetophenone; yield 88%; 1 H NMR (400MHz, CDCl 3 )δ: 7.73–7.30 (m, 4H, benzene ring), 4.47 (q, J=7.1Hz, 2H, OCH 2 ), 2.64 (s, 3H, CH 3 ), 1.45(t, J=7.1Hz, 3H, CH 3 ).

Embodiment 3

[0058] Electrooxidative Preparation of Methyl 2-Methylacetophenone

[0059]

[0060] The anode of the electrolytic cell is carbon felt (10×10×2mm 3 ), the cathode is platinum mesh (10×10×2mm 3 ), a magnetic stirrer was added to the tank; 0.5mmol (0.082g) methyl 2-methylphenylacetate, 1.0mmol (0.163g) N-hydroxyphthalimide 0.15mmol 2,6-dimethyl Pyridine and 1mmol (0.342g) tetrabutylammonium perchlorate were added to the electrolytic cell, 9.5mL acetonitrile and 0.5mL water were dissolved, electrolyzed at a constant current of 5mA under an oxygen atmosphere at 60°C, and the reaction was stopped when the cell voltage reached 3.0V, and the reaction solution After vacuum distillation and drying, ethyl acetate was dissolved, washed three times with water, and the organic layer was dried over anhydrous sodium sulfate to obtain 0.069 g of methyl 2-methylacetophenone; the yield was 78%; 1 H NMR (400MHz, CDCl 3 )δ: 7.71–7.65 (m, 1H, benzene ring), 7.49 (d, J=5.3Hz, 1H, benzene ring...

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Abstract

The present invention relates to the electrooxidative preparation method of methyl acetophenone ester shown in formula I, and its preparation reaction is as follows: the methyl group is selected from: 2-methyl, 3-methyl or 4-methyl; R is selected from: methyl , Ethyl. The electrooxidation preparation method is to install an anode working electrode and a cathode in a non-diaphragm electrolytic cell, and use methyl phenylacetate, phthalimide derivatives, organic solvents, alkalis and electrolytes as electrolytes; At a certain temperature, constant current electrolysis for a certain time, electrooxidation reaction to obtain methyl acetophenone ester (I). Among them, the electrooxidative preparation method of 2-methylacetophenone methyl ester can be used to prepare kresoxim-methyl and trifloxystrobin.

Description

technical field [0001] The invention relates to a compound preparation method, in particular to a new preparation method of kresoxim-methyl and trifloxystrobin; in particular, an electro-oxidative preparation method of the key intermediate 2-methylacetophenone methyl ester. Background technique [0002] Kresoxim-methyl (kresoxim-methyl, also known as phenoxythrin, phenoxystrobin, II) chemical name: (E)-2-methoxyimino-(2-(o-methylphenoxymethyl)benzene base) methyl acetate. Trifloxystrobin (trifloxystrbin, trade name Flint, Ⅲ) chemical name: (E,E)-2-methoxyimino-2-[2-[[1-[3-(trifluoromethyl)phenyl] Ethyleneamino]oxymethyl]phenyl]methyl acetate: [0003] [0004] There are many preparation methods of kresoxim-methyl and trifloxystrobin, most of which are through the key intermediate of methyl 2-methylacetophenone; the preparation methods of methyl 2-methylacetophenone are summarized as follows: [0005] U.S. Patent [US 5145980,1992] selects o-methylbenzaldehyde to obtain ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/12C25B3/23C25B3/07
CPCC25B3/23C25B3/07
Inventor 胡艾希徐雷涛李康明
Owner 湖北中迅长青科技有限公司
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