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Method for synthesizing prohexadione calcium and trinexapac-ethyl

A synthesis method and procyclonic acid calcium technology are applied in chemical instruments and methods, preparation of carboxylic acid esters, preparation of organic compounds, etc., which can solve the problems of long reaction time, increased system pressure, and increased risk, and achieve synthesis conditions. Simple, simple and safe operation, convenient for industrial amplification effect

Active Publication Date: 2017-09-15
鹤壁全丰生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The whole reaction process not only consumes a large amount of heat energy and causes the pressure of the system to rise, but also requires the reaction kettle to be able to withstand pressure, and the reaction time is too long, resulting in high cost and increased risk

Method used

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  • Method for synthesizing prohexadione calcium and trinexapac-ethyl
  • Method for synthesizing prohexadione calcium and trinexapac-ethyl
  • Method for synthesizing prohexadione calcium and trinexapac-ethyl

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Experimental program
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Effect test

Embodiment 1

[0043] Embodiment 1, the synthesis of prohexadione calcium

[0044] Carry out according to following reaction equation:

[0045]

[0046] (1) Synthesis of compound shown in formula Ⅱ

[0047] Get 50g diethyl maleate and 50mL absolute ethanol in the 500mL reaction flask, add dropwise 20% (mass fraction) ethanol solution 98g of sodium ethylate at room temperature (the mol ratio of diethyl maleate and sodium ethylate is 1 : 1), the dropwise addition was completed in 5 minutes, followed by room temperature (20° C.) for 1 hour. The crude product of the compound represented by formula II can be obtained after the liquid phase detection of the raw material disappears completely.

[0048] According to the following NMR characterization data, the structure of the obtained compound is correct:

[0049] 1 H NMR (400MHz, CDCl 3 )δ4.33–4.11 (m, 5H), 3.73 (dq, J=14.1, 7.0Hz, 1H), 3.52 (dq, J=14.1, 7.0Hz, 1H), 2.74 (qd, J=15.9, 6.6Hz ,2H),1.34–1.17(m,9H).

[0050] (2) Synthesis of ...

Embodiment 2

[0063] Embodiment 2, the synthesis of trinexapac-ethyl

[0064] Carry out according to following reaction equation:

[0065]

[0066] (1) Synthesis of compound shown in formula Ⅱ

[0067] Get 50g diethyl maleate and 50mL absolute ethanol in the 500mL reaction flask, add dropwise 20% (mass fraction) ethanol solution 98g of sodium ethylate at room temperature (the mol ratio of diethyl maleate and sodium ethylate is 1 : 1), the dropwise addition was completed in 5 minutes, followed by room temperature (20° C.) for 1 hour. The crude product of the compound represented by formula II can be obtained after the liquid phase detection of the raw material disappears completely.

[0068] According to the following NMR characterization data, the structure of the obtained compound is correct:

[0069] 1 H NMR (400MHz, CDCl 3 )δ4.33–4.11 (m, 5H), 3.73 (dq, J=14.1, 7.0Hz, 1H), 3.52 (dq, J=14.1, 7.0Hz, 1H), 2.74 (qd, J=15.9, 6.6Hz ,2H),1.34–1.17(m,9H).

[0070] (2) Synthesis of comp...

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Abstract

The invention discloses a method for synthesizing prohexadione calcium and trinexapac-ethyl. The method comprises the following steps: reacting diethyl maleate (alpha, beta unsaturated carboxylic acid) with sodium ethoxide to obtain high-purity intermediate compound as shown in a formula II, and preparing prohexadione calcium and trinexapac-ethyl from the compound as shown in the formula II. In the reacting steps for preparing the compound as shown in the formula II, sodium ethoxide serving as a reactant participates in the reaction rather than a strong basic catalyst; a 1,3-cyclohexanedione compound is prepared from the intermediate compound as shown in the formula II and acetone under a reflux condition, and the total yield for the reaction of two steps can be 87 percent. The method has the advantages of low energy consumption, short reaction time, easy operation and the like by using the 1,3-cyclohexanedione compound as the intermediate, and can be used for preparing prohexadione calcium and trinexapac-ethyl with high yield.

Description

technical field [0001] The invention relates to a synthesis method of prohexadione calcium and trinexapac-ethyl, belonging to the field of organic synthesis. Background technique [0002] Calcium prohexadione (calcium 3,5-dioxo-4-propionylcyclohexanecarboxylate), is a new type of plant growth regulator first developed by Japan Combination Chemical Industry Company, belonging to acylcyclohexane A diketone growth retardant, it works by interfering with the final step of gibberellin biosynthesis, that is, blocking the synthesis of GA12 aldehyde to GA8 acid, hindering the activation process of gibberellin, and making abscisic acid, corn The level of cytokinin and isopentenyl adenosine increases, which can inhibit the growth of shoots, promote reproductive growth, achieve the purpose of increasing production and improving quality, and has better disease resistance. It works by soaking seeds, watering, and spraying. Compared with the currently widely used triazole retardants, pro...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/757
CPCC07C67/31C07C67/313C07C67/343C07C69/708C07C69/757
Inventor 张朋飞王敬军王聚强陈云生谢三星徐雪松
Owner 鹤壁全丰生物科技有限公司
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