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Method for synthesizing flocumafen intermediate

A synthesis method and an intermediate technology, which are applied in the field of synthesis of the anticoagulant rodenticide flumarinone intermediate, can solve the problems of increased cost, harsh reaction conditions, and large pollution, and achieve the avoidance of harsh requirements, simple and effective method, and The effect of mild reaction conditions

Active Publication Date: 2011-05-25
江苏功成生物科技有限公司
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  • 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
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Effect test

Embodiment 1

[0035] Take 10.8g of 3-benzyl-3-p-methoxyphenylpropionic acid, dissolve it in 250mL of toluene to obtain a mixed solution, add 15.8g of benzenesulfonic acid to the mixed solution, and reflux for 12h. After the reaction is completed, the organic solvent is evaporated to obtain Residue, after cooling the residue to room temperature, add 60 mL of ethyl acetate to dissolve, then wash with water and 10% sodium carbonate solution in sequence, separate the organic phase, evaporate the solvent in the organic phase, and finally recrystallize with methanol , 7.2 g of 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one were obtained, with a yield of 71%. mp (melting point) 102-105°C.

[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 10.8g of 3-benzyl-3-p-methoxyphenylpropionic acid, dissolve it in 300mL of dichloroethane, add 4.6g of trifluoroacetic acid, and reflux for 20h. After the reaction is completed, the organic solvent is evaporated to obtain a residue. The mixture was cooled to room temperature, dissolved in 100 mL of ethyl acetate, and washed with water and 10% sodium carbonate solution in sequence. Separate the organic phase, evaporate the solvent in the organic phase, and recrystallize methanol to obtain 6.6 g of 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one with a yield of 65%. . mp 101-103°C.

[0039] Analysis data is with embodiment 1.

Embodiment 3

[0041] Take 10.8g of 3-benzyl-3-p-methoxyphenylpropionic acid, dissolve it in 250mL of xylene, add 19.6g of trichloroacetic acid, and reflux for 5h. After the reaction is completed, the organic solvent is evaporated to obtain a residue, and the residue is cooled After reaching room temperature, 100 mL of ethyl acetate was added to dissolve, followed by washing with water and 10% sodium carbonate solution. Separate the organic phase, evaporate the solvent in the organic phase, and recrystallize methanol to obtain 7.0 g of 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one with a yield of 69%. . mp 101-103°C.

[0042] Analysis data is with embodiment 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 the intermediate of the anticoagulant rodenticide fluocinone, specifically a key intermediate of fluocinone, 3-p-methoxyphenyl-1,2,3,4-tetrahydro Synthetic 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 mice. Its chemical structural formula (II) is as shown in the following formula Show: [0003] [0004] 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one (I) is a key intermediate for the synthesis of the second-generation anticoagulant rodenticide flumarinone. [0005] [0006] Existing domestic and foreign methods of synthesizing flumarone (II) can roughly be divided into two kinds: [0007] Method 1, using p-methoxycinnamate as raw material, r...

Claims

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Application Information

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IPC IPC(8): C07C49/637C07C45/66
Inventor 姚志牛
Owner 江苏功成生物科技有限公司
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