Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis methods of flocumafen and flocumafen intermediate

A synthesis method and intermediate technology, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve problems such as poor repeatability of the method, low product purity, and long reaction time, etc., to achieve the method Simple and effective, good atom economy, easy to react and controllable effect

Active Publication Date: 2013-06-05
江苏功成生物科技有限公司
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction yield of the above method is low, the purity of the obtained product is not high, and there are problems such as poor repeatability of the method, or too long reaction time
The above method can only be used for laboratory research and small batch production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis methods of flocumafen and flocumafen intermediate
  • Synthesis methods of flocumafen and flocumafen intermediate
  • Synthesis methods of flocumafen and flocumafen intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035](1) Synthesis of 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one (compound of formula III)

[0036] Take 10.8g of 3-benzyl-3-p-methoxyphenylpropionic acid (compound of formula II), dissolve it in 250mL of toluene to obtain a mixed solution, add 15.8g of benzenesulfonic acid to the mixed solution, reflux for 12h, and the reaction is complete. Evaporate the solvent to obtain the residue, add 60 mL of ethyl acetate to dissolve the residue after cooling to room temperature, then wash with water and 10% sodium carbonate solution in order, separate the organic phase, evaporate the solvent in the organic phase, and finally Recrystallized from methanol to obtain 7.2 g of 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one (compound of formula III), with a yield of 71%. mp (melting point) 102-105°C.

[0037] 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=8.0Hz, 1H).

[0038] (2) Synthesis of 3-p...

Embodiment 2

[0049] (1) Synthesis of 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one (compound of formula III)

[0050] Take 10.8g of 3-benzyl-3-p-methoxyphenylpropionic acid (compound of formula II), dissolve it in 300mL of dichloroethane, add 4.6g of trifluoroacetic acid, reflux for 20h, after the reaction is completed, evaporate the solvent to obtain Residue, the residue was cooled to room temperature, dissolved in 100 mL of ethyl acetate, washed with water and 10% sodium carbonate solution in sequence. The organic phase was separated, the solvent in the organic phase was evaporated, and methanol was recrystallized to obtain 6.6 g of 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one (compound of formula III), The yield is 65%. mp101-103°C.

[0051] Analysis data is with embodiment 1.

[0052] (2) Synthesis of 3-p-hydroxyphenyl-1,2,3,4-tetralin-1-one (compound of formula IV)

[0053] 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one (compound of formula III) was subjected to demethylation reacti...

Embodiment 3

[0062] (1) Synthesis of 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one (compound of formula III)

[0063] Take 10.8g of 3-benzyl-3-p-methoxyphenylpropionic acid (compound of formula II), dissolve it in 250mL of xylene, add 19.6g of trichloroacetic acid, and reflux for 5h. After the reaction is complete, evaporate the solvent to obtain a residue , the residue was cooled to room temperature, dissolved in 100 mL of ethyl acetate, washed with water and 10% sodium carbonate solution in sequence. The organic phase was separated, the solvent in the organic phase was evaporated, and methanol was recrystallized to obtain 7.0 g of 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one (compound of formula III), The yield was 69%. mp101-103°C.

[0064] Analysis data is with embodiment 1.

[0065] (2) Synthesis of 3-p-hydroxyphenyl-1,2,3,4-tetralin-1-one (compound of formula IV)

[0066] 3-p-methoxyphenyl-1,2,3,4-tetralin-1-one (compound of formula III) was subjected to demethylation reaction to obtain c...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses synthesis methods of flocumafen and a flocumafen intermediate. The synthesis method of the flocumafen intermediate comprises the following steps of: dissolving 3-benzyl-3-methoxy phenyl propionic acid in an organic solvent; adding an acid medium; performing a reflux reaction; boiling the solvent off; adding ethyl acetate to dissolve residues; and performing posttreatment so as to obtain an intermediate, namely 3-methoxy phenyl-1,2,3,4-tetrahydronaphthalene-1-ketone. The synthesis method of the flocumafen is an improvement on a method for preparing the intermediate, namely 3-methoxy phenyl-1,2,3,4-tetrahydronaphthalene-1-ketone by cyclization and a method for preparing an intermediate, namely 3-(4-trifluoromethyl benzyloxy phenyl-4-radical)-1,2,3,4-tetrahydronaphthalene-1-ketone by an ether synthesis method. The synthesis methods are simple, effective and environmentally-friendly, and are easy to operate; a reaction condition is mild; a product is easy to separate, has high purity and good atom economy; and the cost of an entire reaction is greatly lowered, a small quantity of three wastes is produced and the synthesis methods are suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of rodenticide and its intermediate, specifically a kind of fluocorone and its intermediate 3-(4-trifluoromethylbenzyloxyphenyl-4-yl)-1,2 , The synthetic method of 3,4-tetrahydronaphthalene-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 is a second-generation anticoagulant rodenticide, which can effectively kill resistant mice. Its chemical structural formula (I) is as follows Show: [0003] [0004] European patent EP0098629 discloses a common method for preparing intermediate 3-p-hydroxyphenyl-1,2,3,4-tetralin-1-one (compound of formula IV), and its reaction route is as follows: [0005] [0006] This route uses polyphosphoric acid (PPA) when preparing 3-p-methoxyphenyl-1,2,3,4-tetrahydronaphthalene-1-one (compound of formula III) by cyclization, and its con...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/56C07C49/755C07C45/64
Inventor 姚志牛赵青霞朱长武
Owner 江苏功成生物科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com