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Preparation method of prohexadione calcium intermediate

A technology of prohexadione calcium and intermediates, which is applied in the field of preparation of prohexadione calcium intermediates, can solve the problems of low atom economy, many reaction steps and the like, and achieves the effects of easy industrialization, simple operation and convenient post-processing process.

Pending Publication Date: 2022-07-29
ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] This process avoids the use of propanol, but has the lowest atom economy, produces a large amount of solid waste, and has many reaction steps

Method used

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  • Preparation method of prohexadione calcium intermediate
  • Preparation method of prohexadione calcium intermediate
  • Preparation method of prohexadione calcium intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 182 grams of ethyl 3,5-dihydroxybenzoate into a 500ml stainless steel reaction kettle, add 182 grams of tetrahydrofuran, 92 grams of formic acid, add 1.82 grams of Raney nickel, close the reaction kettle, it cannot be opened during the process, and the temperature is raised to 100 ° C , and reacted for 10 hours. After the reaction was completed, it was cooled to 20 °C, 1.80 g of Raney nickel was recovered by filtration, and 180 g of tetrahydrofuran was recovered by rotary evaporation to obtain 176 g of ethyl 3,5-dioxohexylcarboxylate. The yield was 95.6%. HPLC Content 98.7%.

[0037] Product H NMR spectrum (CDCl3) δ: 1.2-1.3 (3H, CH 3 ),2.6-2.7(1H,CH),2.5-3.0(4H,CH2,CH2),3.58-3.62(2H,CH 2 ), 4.1-4.3 (2H,CH 2 ).

[0038] Elemental Analysis: Carbon 58.7%, Hydrogen 6.6%, Oxygen 34.7%.

[0039] Main fragment peaks MS(m / z): 184(M+), 139(M-OC2H5), 111(M-COOC2H5), 69(M-C6H11O2), 41(M-C7H11O3), 29(M-C8H10O5 )

[0040] Identified as ethyl 3,5-dioxohexylcarboxylate.

Embodiment 2

[0042] Add 182 grams of ethyl 3,5-dihydroxybenzoate to a 1500ml stainless steel reaction kettle, add 364 grams of methanol, 460 grams of formic acid, add 9.1 grams of Raney nickel, close the reaction kettle, it cannot be opened during the process, and the temperature is raised to 150 ° C , and reacted for 24 hours. After the reaction was completed, it was cooled to 30° C., 9.0 grams of Raney nickel was recovered by filtration, 360 grams of methanol and 300 grams of formic acid were recovered by rotary evaporation, and 176 grams of ethyl 3,5-dioxohexyl formate were obtained in a yield of 176 grams. 96.7%, HPLC content 98.0%.

Embodiment 3

[0044] Add 182 grams of ethyl 3,5-dihydroxybenzoate into a 1500ml stainless steel reactor, add 300 grams of ethanol, 100 grams of formic acid, add 5.0 grams of Raney nickel, close the reactor, and it cannot be opened during the process, and the temperature is raised to 120 ° C , reacted for 12 hours, after the reaction was completed, cooled to 25 ° C, 4.8 g of Raney nickel was recovered by filtration, and 290 g of ethanol was recovered by rotary evaporation to obtain 174 g of ethyl 3,5-dioxohexylcarboxylate with a yield of 95.6%. HPLC Content 98.1%.

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Abstract

The invention discloses a preparation method of a prohexadione calcium intermediate. The method comprises the following steps: dissolving 3, 5-ethyl dihydroxybenzoate in a solvent, adding formic acid and a catalyst, heating to 100-150 DEG C for reaction, cooling to 20-30 DEG C after the reaction is finished, filtering to recover the catalyst, and carrying out reduced pressure evaporation on filtrate to recover unreacted formic acid and the solvent, thereby obtaining the 3, 5-dioxocyclohexyl ethyl formate. According to the process, acetone is not used, a large amount of waste salt is not generated, and the process is environment-friendly, high in yield and purity and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of a prohexadione calcium intermediate, which belongs to the technical field of pesticide synthesis. Background technique [0002] Plant growth regulators are a class of pesticides used to regulate plant growth and development, including synthetic compounds with similar effects to natural plant hormones and natural plant hormones extracted from organisms. Prohexadione calcium is a new type of cyclohexenone plant growth regulator, its common name is: prohexadione-Calcium. The chemical name is: calcium 3,5-dioxo-4-propionylcyclohexene carboxylate. The English name is: Calcium 3,5-dioxo-4-propionylcyclohexanecarboxylic acid. [0003] The structural formula is: [0004] [0005] The role of prohexadione is mainly used to control the growth of cereal crops, which can shorten the length of crop stems, and can enhance the plant's disease resistance, cold resistance, and stress resistance, and has obvious ant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/313C07C69/757
CPCC07C67/313C07C69/757
Inventor 蒋成君徐大国
Owner ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY
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