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Synthetic method for bactericide tebuconazole

A synthetic method, the technology of tebuconazole, which is applied in the field of synthesis of the fungicide tebuconazole, can solve the problems of isomers and low product yield, and achieve the effect of no by-products and mild reaction

Inactive Publication Date: 2015-04-22
QINGDAO WUWEI THERMAL INSULATION MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, a strong base is used to remove the H at the alpha position of pinacolone, but the yield of the product is not high, and there are isomers

Method used

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  • Synthetic method for bactericide tebuconazole
  • Synthetic method for bactericide tebuconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 4,4-dimethyl-1-(4-chlorophenyl)-1-penten-3-one:

[0031] Add sodium methoxide, 2mol p-chlorobenzaldehyde, 1mol pinaconone and 1mol potassium bicarbonate with a mass concentration of 55% to the reaction flask, stir and heat up to 55°C, reflux at this temperature for 2h; heat up to 70°C and keep for 1.5h, Then cool to room temperature and filter to obtain 4,4-dimethyl-1-(4-chlorophenyl)-1-penten-3-one; the yield is 98.9%, and the purity is 99.4%;

Embodiment 2

[0033] Identical with embodiment 1 operating steps, difference is that weakly basic catalyst is sodium bicarbonate; Productive rate is 99.4%, and purity is 99.5%;

Embodiment 3

[0035] Synthesis of 4,4-Dimethyl-1-(4-chlorophenyl)-3-pentanone

[0036] 4,4-dimethyl-1-(4-chlorophenyl)-1-penten-3-one 4mol obtained in Example 2 was put into a hydrogenation kettle, the solvent methanol was added, and then 2mol of platinum oxide and Lu Hong 1 mol of the solution; replaced with nitrogen three times and hydrogen three times successively, then heated up to 65°C, and at this temperature, hydrogen was introduced at a pressure of 3.0 MPa until the reaction stopped absorbing hydrogen, and the reaction solution was lowered to normal temperature and normal temperature. pressure, and the filtrate was distilled under reduced pressure to remove the solvent to obtain 4,4-dimethyl-1-(4-chlorophenyl)-3-pentanone; the yield was 99.5%, and the purity was 99.3%;

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Abstract

A disclosed synthetic method for bactericide tebuconazole comprises steps of synthesis of 4,4-dimethyl-1-(4-chlorophenyl)-1-penten-3-one, synthesis of 4,4-dimethyl-1-(4-chlorophenyl)-3-pentanone, preparation of 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)-oxirane, and synthesis of tebuconazole. The synthetic method is mild in reaction and free of by-product during reaction, and the product has the yield of 90.1% and the purity of 99.5%.

Description

technical field [0001] The invention relates to a method for synthesizing a fungicide tebuconazole, which belongs to the field of fine chemicals. Background technique [0002] Tebuconazole, the chemical name is (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)penta- 3-alcohol, the structure of which is shown in formula (I). Tebuconazole is a high-efficiency, broad-spectrum, systemic triazole fungicidal pesticide, which has three functions of protection, treatment and eradication, and has a wide bactericidal spectrum and long-lasting effect. long. [0003] [0004] There are many studies on the synthesis of tebuconazole, most of which use p-chloroformaldehyde as the starting material to prepare tebuconazole through steps such as aldehyde and ketone condensation, catalytic hydrogenation, epoxidation reaction and ring-opening reaction. For example, Tan Chengxia et al. reported that p-chlorobenzaldehyde and pinacolone were used as raw materials to syn...

Claims

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Application Information

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IPC IPC(8): C07D249/08
CPCC07D249/08
Inventor 李本明
Owner QINGDAO WUWEI THERMAL INSULATION MATERIAL
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