Synthesis method of 2,4-dichlorophenyl acetaldehyde

A technology of dichlorophenylacetaldehyde and synthesis method, which is applied in the preparation of heterocyclic compounds, organic chemistry, etc., can solve the problems of reducing the content of 2,4-dichlorophenylacetaldehyde, increase the content and yield, and avoid side effects. Response, cost reduction effect

Active Publication Date: 2013-03-27
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, ethyl chloroacetate and 2,4-dichlorobenzaldehyde are usually used to prepare under the catalysis of sodium alkoxide. However, because the chlorine atom in ethyl chloroacetate easily reacts with sodium alkoxide, it is easy to eventually lead to 2, 4-Dichlorophenylacetaldehyde content decreased

Method used

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  • Synthesis method of 2,4-dichlorophenyl acetaldehyde
  • Synthesis method of 2,4-dichlorophenyl acetaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of synthetic method of 2,4-dichlorophenylacetaldehyde, its concrete steps are:

[0026] (1) Closed loop

[0027] Add 118.9g of sodium methoxide solution (5% mass fraction) to 50ml of methanol, stir evenly, add 17.5g of 2,4-dichlorobenzaldehyde, stir until completely dissolved, then add 14.3g of ethyl acetoacetate dropwise, drop After completion, the reaction was carried out at 60° C., followed by TLC until the reaction was complete. After filtration, the filtrate was cooled to -5° C. for crystallization, and 22.7 g of solid intermediate I was obtained by suction filtration, with a content of 85% and a yield of 87%.

[0028] (2) Alkaline hydrolysis

[0029] Add 34.6g potassium carbonate aqueous solution (mass fraction: 20%) to 13.1g intermediate product I, keep the temperature at 20°C for reaction, TLC tracking detection until the reaction is complete;

[0030] (3) Acid adjustment

[0031] The above-mentioned completely reacted solution was lowered to room temp...

Embodiment 2

[0035] A kind of synthetic method of 2,4-dichlorophenylacetaldehyde, its concrete steps are:

[0036] (1) Closed loop

[0037] Add 907g of sodium ethoxide solution (mass fraction: 15%) to 200ml of ethanol, stir evenly, add 175g of 2,4-dichlorobenzaldehyde, stir until completely dissolved, then add 390g of ethyl acetoacetate dropwise, dropwise, 40 ℃ heat preservation reaction, TLC tracking detection until the reaction is complete, filter, the filtrate is cooled to -5 ℃ for crystallization, suction filtration to obtain 229.8 g of solid intermediate product I, the content is 83%, and the yield is 88%.

[0038] (2) Alkaline hydrolysis

[0039] Add 212.7g of sodium carbonate aqueous solution (5% mass fraction) to 13.1g of intermediate product I, keep the reaction at 40°C, and track and detect by TLC until the reaction is complete;

[0040] (3) Acid adjustment

[0041] The above-mentioned fully reacted solution was lowered to room temperature, acidified with acetic acid until the...

Embodiment 3

[0045] A kind of synthetic method of 2,4-dichlorophenylacetaldehyde, its concrete steps are:

[0046] (1) Closed loop

[0047] Add 123.1g of sodium isopropoxide solution (mass fraction: 10%) to 80ml of isopropanol, stir evenly, add 17.5g of 2,4-dichlorobenzaldehyde, stir until completely dissolved, then add dropwise 26g of ethyl acetoacetate Ester, dripping, 50 ℃ heat preservation reaction, TLC tracking detection until the reaction is complete, filtration, the filtrate cooled to -5 ℃ crystallization, suction filtration to obtain 22.5g of solid intermediate product I, the content is 81%, the yield is 86%.

[0048] (2) Alkaline hydrolysis

[0049] Add 63.2g sodium bicarbonate aqueous solution (mass fraction is 10%) to 13.1g intermediate product I, 30 DEG C of heat preservation reaction, TLC track detection until reaction is complete;

[0050] (3) Acid adjustment

[0051] The above-mentioned fully reacted solution was lowered to room temperature, acidified with hydrochloric ac...

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Abstract

The invention belongs to the technical field of organic synthesis, and more particularly relates to a synthesis technology of a pesticide intermediate, and in particular relates to a synthesis method of a tetraconazole-related key intermediate, namely 2, 4-dichlorophenyl acetaldehyde. The synthesis method comprises a closed-loop process, an alkaline hydrolysis process, an acidity adjusting process and a decarboxylation process. According to the invention, in the closed-loop process, generally-used ethyl chloroacetate is substituted by ethyl acetoacetate, so that the problem that chlorine ions are easily subjected to side reaction with sodium alcoholate is effectively solved, the content and yield of the finial product are improved, and therefore the cost is reduced.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to the synthesis technology of pesticide intermediates, in particular to the synthesis method of 2,4-dichlorophenylacetaldehyde, a key intermediate of tetrafluconazole. Background technique [0002] English name tetraconazole, chemical name: (RS)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl-1 ,1,2,2-tetrafluoroethyl ether, colorless viscous liquid (the original drug is yellow to brownish yellow liquid). [0003] Tetrafluconazole belongs to triazole fungicides. It is a new type of environmentally friendly pesticide with high efficiency, low toxicity and wide application range. It has good systemic properties, can be quickly absorbed by plants, and conducts internally. Good protective and therapeutic activity, lasting for 6 weeks, suitable for cereal crops, vegetables, etc. Tefluconazole can prevent and control the diseases caused by powdery mildew, Puccinia, Coryza...

Claims

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Application Information

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IPC IPC(8): C07C45/58C07C47/24C07D301/02C07D303/48
Inventor 陈志敏吴文雷张建林史庆苓马韵升高洪奎
Owner JINGBO AGROCHEM TECH CO LTD
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