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Method for preparing trinexapac-ethyl

A technology of trinexapac-ethyl and diethyl succinate, which is applied in the preparation of carboxylic acid esters, the preparation of organic compounds, chemical instruments and methods, etc., and can solve problems such as low product purity, low yield, and harsh reaction conditions , to achieve the effect of high yield, good product purity and mild reaction

Inactive Publication Date: 2011-06-22
张家港田由新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Some synthetic steps in the above synthetic method have the disadvantages of low yield, harsh reaction conditions or low product purity.

Method used

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  • Method for preparing trinexapac-ethyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Step 1, the synthesis of 2-acetone-1,4-diethyl succinate

[0026] Put diethyl maleate (1800.0 g, 10.45 mol), acetone (6000 mL) and diethylamine (149.9 g, 2.07 mol) into a 10 L autoclave, heat to 160 °C, keep the reaction for 24 hours, and cool to room temperature , Atmospheric pressure distillation to remove low boilers, and then oil pump maximum vacuum vacuum distillation to collect fractions at 120-140 ℃ to obtain light yellow liquid diethyl 2-acetone-1,4-succinate with a yield of 89.2%;

[0027] Step 2, the synthesis of 3-ethoxycarbonyl-5-oxocyclohex-1-en-1-alcohol sodium

[0028] Diethyl 2-acetone-1,4-butanedioate (200.0 g, 0.87 mol) was added dropwise to the reaction solution twice, and the temperature was controlled at 30-60 °C. First, 40.0 g was added dropwise. 90 ℃, add the remaining 160.0 g dropwise, after the dropwise addition, the reaction solution was stirred at 80~90 ℃ for 30~45 minutes, TLC detection, the raw material 2-acetone-1,4-diethyl succinate disa...

Embodiment 2

[0036] Step 1, the synthesis of 2-acetone-1,4-diethyl succinate

[0037] Put diethyl maleate (1800.0 g, 10.45 mol), acetone (6200 mL) and diethylamine (149.9 g, 2.07 mol) into a 10 L autoclave, heat to 165 °C, keep the reaction for 26 hours, and cool to room temperature , Atmospheric pressure distillation to remove low boilers, and then oil pump maximum vacuum vacuum distillation to collect 120 ~ 140 ℃ distillate to obtain light yellow liquid 2-acetone-1,4-diethyl succinate with a yield of 90.1%;

[0038] Step 2, the synthesis of 3-ethoxycarbonyl-5-oxocyclohex-1-en-1-alcohol sodium

[0039] Diethyl 2-acetone-1,4-butanedioate (150.0 g, 0.65 mol) was added dropwise to the reaction solution twice, and the temperature was controlled at 30-60 °C. First, 30.0 g was added dropwise. After the dropwise addition, heated to 80-90 °C, stirred for 0.5 hours, and kept at 80-90 °C ℃, add the remaining 120.0 g dropwise, after the dropwise addition is complete, the reaction solution is stirr...

Embodiment 3

[0047] Step 1, the synthesis of 2-acetone-1,4-diethyl succinate

[0048] Put diethyl maleate (1800.0 g, 10.45 mol, 60wt.%), acetone (6315 mL) and diethylamine (149.9 g, 2.07 mol) into a 10 L autoclave, heat to 162 °C, and keep the temperature for 26 hours , cooled to room temperature, atmospheric distillation to remove low boilers, and then oil pump maximum vacuum vacuum distillation to collect 120 ~ 140 ℃ distillate to obtain light yellow liquid 2-acetone-1,4-diethyl succinate, the yield is 91.2%.

[0049] Step 2, the synthesis of 3-ethoxycarbonyl-5-oxocyclohex-1-en-1-alcohol sodium

[0050] Diethyl 2-acetone-1,4-butanedioate (600.0 g, 2.60 mol) was added dropwise to the reaction liquid twice, and the temperature was controlled at 30-60 °C. First, 120.0 g was added dropwise. ℃, add the remaining 480.0 g dropwise, after the dropwise addition is complete, the reaction solution is stirred at 80~90°C for 30~45 minutes, TLC detection, the raw material 2-acetone-1,4-diethyl succ...

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Abstract

The invention discloses a method for preparing trinexapac-ethyl, which comprises the following steps of: performing high pressure condensation on diethyl maleate and acetone serving as raw materials in the presence of diethylamine to obtain 2-acetone-1,4-succinic acid diethyl ester; forming a ring in the presence of sodium hydride to obtain 3-ethoxycarbonyl-5-oxocyclohexyl-1-ene-1-sodium alkoxide; reacting with cyclopropanecarboxylic acid chloride to obtain 3-ethoxycarbonyl-5-oxocyclohexyl-1-ene-1-cyclopropanecarboxylic acid ester alkoxide; and rearranging in the presence of cyanide and triethylamine to obtain the trinexapac-ethyl. The method has the advantages of high yield, mild reaction and high product purity, and is suitable for small-scale laboratorial preparation and industrial production.

Description

technical field [0001] The invention relates to a preparation method of trinexapac-ethyl, a high-efficiency plant growth regulator of cyclohexanedicarboxylic acids. Background technique [0002] Trinexapac-ethyl is a plant growth regulator and an inhibitor of gibberellin biosynthesis, which controls the vigorous growth of plants by reducing the content of gibberellin. Trinexapac-ethyl can be quickly absorbed by plant stems and leaves, and has little absorption by roots, so it can be used on a variety of crops. The latest preparation method of trinexapac-ethyl: Zhejiang University's patent and literature with publication number CN 180776A, "Pesticides", August 2006, Volume 45, Issue 8, p535. Some of the synthetic steps in the above synthetic methods have the disadvantages of low yield, harsh reaction conditions or low product purity. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a method for preparing trinexap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C67/333
Inventor 刘林密
Owner 张家港田由新材料科技有限公司
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