Electrooxidation preparation method of kresoxim-methyl and trifloxystrobin intermediates

An electro-oxidation and electrolytic cell technology, applied in the electrolysis process, electrolysis components, electrolytic organic production, etc., can solve the problems of harsh conditions and complex reaction process, and achieve the effect of simplifying the process flow and reducing the production cost.

Active Publication Date: 2021-08-27
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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  • Electrooxidation preparation method of kresoxim-methyl and trifloxystrobin intermediates
  • Electrooxidation preparation method of kresoxim-methyl and trifloxystrobin intermediates
  • Electrooxidation preparation method of kresoxim-methyl 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 invention relates to an electrooxidation preparation method of methyl acetophenone acid ester as shown in a formula I. The preparation reaction is as follows: methyl is selected from 2-methyl, 3-methyl or 4-methyl; and R is selected from methyl and ethyl. The electrooxidation preparation method comprises the following steps: in a non-diaphragm electrolytic cell, installing an anode working electrode and a cathode, and taking methyl phenylacetate, a phthalimide derivative, an organic solvent, alkali and electrolyte as electrolyte; and at a certain temperature, carrying out constant-current electrolysis for a certain period of time, and carrying out an electrooxidation reaction to obtain the methyl phenyl ethyl ketone acid ester (I). The electro-oxidation preparation method of the 2-methyl acetophenone acid methyl ester can be used for preparing kresoxim-methyl and trifloxystrobin.

Description

Technical field [0001] The present invention relates to a method for preparing compounds, specifically a new method for preparing tristrostrobin and trifloxystrobin; in particular, an electrooxidative preparation method for its key intermediate 2-methylacetophenolate methyl ester. Background technique [0002] kresoxim-methyl, also known as phenoxythrin, phenoxystrobin, Ⅱ, chemical name: (E)-2-methoxyimino-(2-(o-methylphenoxymethyl)benzene base) methyl acetate. 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 for tristrostrobin and trifloxystrobin, most of which are through the key intermediate of methyl 2-methylacetophenonate; the preparation methods of methyl 2-methylacetophenonate are summarized as follows: [0005] U.S. Patent [US 5145980,1992] selects o-tolyl benzaldehyde to undergo cyanation and sodium ...

Claims

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Application Information

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IPC IPC(8): C25B3/23C25B3/07
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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