Chemical method for sythesizing dipheny ether compound

A technology of diphenyl ethers and compounds, which is applied in the field of chemical synthesis of diphenyl ether compounds, can solve the problems of difficult recycling of reaction solvents and catalysts, poisonous and harmful operators, long reaction time, etc., and achieves wide industrial application prospects, The effect of good product quality and convenient operation

Inactive Publication Date: 2004-10-13
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still problems such as too long reaction time, difficult recycling of reaction solvent and catalyst, causing environmental pollution, and reaction solvent being poisonous and harmful to operators.

Method used

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  • Chemical method for sythesizing dipheny ether compound
  • Chemical method for sythesizing dipheny ether compound
  • Chemical method for sythesizing dipheny ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1. Preparation of compound 1

[0023] p-Nitrophenol (0.84g, 6mmol), KOH (0.35g, 82%, 6mmol) and ionic liquid BMImPF 6 (4mL) was successively added into a 20mL double-necked round-bottomed flask, reacted at 60°C for 15 minutes under mechanical stirring, and then added dropwise 2-nitro-4-trifluoromethylchlorobenzene (1.13g, 5 mmol), and reacted for another 2 hours under vigorous stirring. The reaction mixture was extracted with toluene (3 × 10mL), washed once with 10mL of 5% alkali solution, washed with water until neutral, anhydrous MgSO 4 After drying, the solvent was distilled off to obtain compound 1 (1.48 g, yield 82%).

Embodiment 2

[0024] Embodiment 2. preparation compound 2

[0025] p-acetylphenol (0.75g, 5.5mmol), Na 2 CO 3 (0.64g, 99.8%, 6mmol) and ionic liquid HMImPF 6 (4mL) was reacted at 25°C for 5 minutes, and then 2,6-dinitro-4-trifluoromethylchlorobenzene (1.35g, 5mmol) was added in three batches, stirred and reacted at 25°C for 0.5 hour, and the reaction mixture was washed with Extract with toluene (3×10mL), wash once with 10mL of 5% alkali solution, wash with water until neutral, anhydrous MgSO 4 After drying, the solvent was distilled off to obtain compound 2 (1.68 g, yield 91%).

Embodiment 3

[0026] Example 3. Preparation of compound 3

[0027] Phenol (0.48g, 5mmol), NaOH (0.25g, 95%, 6mmol) and ionic liquid EMImCF 3 CO 2 (4mL) was successively added into a 20mL double-necked round-bottom flask, stirred to dissolve most of the raw materials, then added 2-nitro-4-trifluoromethylchlorobenzene (1.13g, 5mmol), and stirred vigorously at 50°C React for 2 hours. Compound 3 (1.11 g, yield 90%) was obtained by a post-treatment method similar to that of Example 1.

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Abstract

The chemical synthesis method of diphenyl ether compound adopts the room temp. ionic liquid formed from N-alkylpyridine cation or 1,3-dialkylimidazole cation and fluorine-containing anion as reaction medium, uses phenol and aromatic halohydrocarbon as reaction mass, and adopts continuous process or one-pot process under the basic condition to synthesize diphenyl ether compound. As compared with traditional synthesis method said invented method has the advantages of moderate reaction condition, short reaction time, high product yield and good quality, etc. Said diphenyl ether compound is a kind is important medicine and pesticide product or organic intermediate body, so that it has extensive application.

Description

technical field [0001] The invention relates to a chemical synthesis method of diphenyl ether compounds. This method is suitable for the synthesis of room temperature ionic liquids composed of N-alkylpyridine cations or 1,3-dialkylimidazolium cations and fluorine-containing anions as reaction media, phenol and aromatic halogenated hydrocarbons as reactants, and under alkaline conditions In the case of diphenyl ether compounds. Background technique [0002] Diphenyl ether compounds are an important class of organic synthesis intermediates or products, which are widely used in the fields of medicine and pesticides. Its traditional synthetic method usually carries out (J.B.Hendrickson, C.Kandall, Tetrahedron Lett., 1970,5,343; R.A.W. Johnstone, M.E. Rose, Tetrahedron, 1979, 35, 2169; A. Mckillop, J.C. Fiaud, R.P. Hug, Tetrahedron, 1974, 30, 1379; H.H. Freedaman, R.A. Duboes, Tetrahedron Lett., 1975, 38, 3251.), sometimes Need to add a small amount of catalysts such as po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/01C07C43/263
Inventor 许丹倩刘宝友徐振元
Owner ZHEJIANG UNIV OF TECH
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