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Method for synthesizing flocumafen intermediate

A synthesis method and intermediate technology are applied in the field of synthesis of the intermediates of anticoagulant rodenticide fluoromarone, can solve the problems of harsh reaction conditions, large pollution, increased cost and the like, and achieve mild reaction conditions, simple and effective methods, Avoid demanding effects

Active Publication Date: 2013-04-24
江苏功成生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0026] Use polyphosphoric acid (PPA) ring closure to prepare 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one (I), the amount of which is 5 to 6 times the molar amount of the reaction raw materials , because polyphosphoric acid is a very viscous liquid, it is inconvenient to measure and use, so the use of a large amount of polyphosphoric acid brings great difficulties to the reaction feeding and post-treatment, and at the same time, the generation of a large amount of phosphorus-containing wastewater brings great harm to the three wastes Handling brings troubles, resulting in heavy workload and increased cost, and is not suitable for large-scale industrial production
[0027] Use SOCl 2 In the ring closure reaction with Lewis acid, the catalysts of Lewis acid generally have the problem of large pollution. In addition, such as Lewis acid aluminum trichloride, etc., are easy to absorb moisture and hydrolyze, and require anhydrous when used, and the reaction conditions are relatively harsh.
In the reaction, toxic and harmful substances such as hydrogen chloride and carbon disulfide are generated, polluting the environment, so it is not suitable for industrial production

Method used

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  • Method for synthesizing flocumafen intermediate
  • Method for synthesizing flocumafen intermediate
  • Method for synthesizing flocumafen intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Take 10.8 g of 3-benzyl-3-p-methoxyphenylpropionic acid and dissolve it with 250 mL of toluene to obtain a mixed solution. Add 15.8 g of benzenesulfonic acid to the mixed solution and react under reflux for 12 hours. After the reaction is complete, the organic solvent is evaporated to obtain The residue is cooled to room temperature and dissolved by adding 60mL ethyl acetate, and then washed with water and sodium carbonate solution with a mass concentration of 10%. The organic phase is separated, the solvent in the organic phase is evaporated, and finally recrystallized with methanol 7.2 g of 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one was obtained with a yield of 71%. mp (melting point) 102~105℃.

[0036] 1 HNMR(500MHz, CDCl 3 )δ: 2.80~3.00(m,2H), 3.18~3.51(m,3H), 3.83(s,3H), 6.93(d, J=8.5Hz, 2H), 7.24~7.55(m,5H), 8.10 (d, J=8.0 Hz, 1H).

Embodiment 2

[0038] Take 10.8 g of 3-benzyl-3-p-methoxyphenylpropionic acid, dissolve it in 300 mL of dichloroethane, add 4.6 g of trifluoroacetic acid, and react under reflux for 20 hours. After the reaction is complete, the organic solvent is evaporated to obtain a residue. The material was cooled to room temperature, and 100 mL of ethyl acetate was added to dissolve it, and then washed with water and a sodium carbonate solution with a mass concentration of 10%. Separate the organic phase, evaporate the solvent in the organic phase, and recrystallize from methanol to obtain 6.6 g of 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one, with a yield of 65% . mp 101~103℃.

[0039] The analysis data is the same as in Example 1.

Embodiment 3

[0041] Take 10.8 g of 3-benzyl-3-p-methoxyphenylpropionic acid, dissolve it in 250 mL of xylene, add 19.6 g of trichloroacetic acid, and react under reflux for 5 hours. After the reaction is complete, the organic solvent is evaporated to obtain a residue, and the residue is cooled To room temperature, add 100 mL of ethyl acetate to dissolve, and wash sequentially with water and a sodium carbonate solution with a mass concentration of 10%. Separate the organic phase, evaporate the solvent in the organic phase, and recrystallize from methanol to obtain 7.0 g of 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one, with a yield of 69% . mp 101~103℃.

[0042] The analysis data is the same as in Example 1.

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Abstract

The invention discloses a method for synthesizing a flocumafen intermediate, which comprises the following steps: obtaining a mixed solution by dissolving 3-phenmethyl-3-p-methoxyphenyl monoprop into organic solvents, adding acid media into the mixed solution, carrying out backflow reaction for 3 to 20h, obtaining residues by steaming out the organic solvents after reaction completion, sequentially using water and sodium carbonate solution with the mass concentration being 10 percent for washing after adding ethyl acetate to dissolve the residues, separating out organic phases, steaming out solvents in the organic phases, obtaining 3-p-methoxyphenyl-1,2,3,4-tetranap-1-ketone crude products, and finally, recrystallizing the crude products by methanol to obtain 3-p-methoxyphenyl-1,2,3,4-tetranap-1-ketone, wherein the molar proportion of the 3-phenmethyl-3-p-methoxyphenyl monoprop to the acid media is 1 / 1 to 3. The method disclosed by the invention is simple, efficient and environment-friendly and is easy to operate, the yield and the purity of products can be improved, and the method is applicable to industrialized production.

Description

Technical field [0001] The present invention relates to a method for synthesizing an intermediate of the anticoagulant rodenticide flurodentone, in particular to a key intermediate 3-p-methoxyphenyl-1,2,3,4-tetrahydro Synthesis method of naphthalene-1-one. Background technique [0002] Flocoumafen, chemical name: 4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-((4-trifluoromethylbenzyloxy)phenyl)- 1-Naphthyl)-2H-1-benzopyran-2-one. It is a second-generation anticoagulant rodenticide, which can effectively kill resistant rats. Its chemical structure (II) is as follows Show: [0003] [0004] 3-P-Methoxyphenyl-1,2,3,4-tetrahydronaphthalen-1-one (I) is a key intermediate for the synthesis of the second generation anticoagulant rodenticide flurdomone. [0005] [0006] The existing domestic and foreign methods for synthesizing fluranone (II) can be roughly divided into two types: [0007] Method 1: Using p-methoxycinnamate as raw material, reacting with Grignard reagent, the resulting compound is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/637C07C45/66
Inventor 姚志牛赵青霞朱长武
Owner 江苏功成生物科技有限公司