Water → Methyl 2-{p-{5-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}propionate

HRID 21509

Reaktionsgleichung

Reaktionsgleichung von HRID 21509
[N+]([C:4]1[CH:5]=[C:6]([O:13][C:14]2[CH:19]=[C:18]([F:20])[C:17]([C:21]([F:24])([F:23])[F:22])=[C:16]([Cl:25])[CH:15]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-])=O.[OH:26][C:27]1[CH:39]=[CH:38][C:30]([O:31][CH:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(Cl)Cl>[Cl:25][C:16]1[CH:15]=[C:14]([O:13][C:6]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH:5]=2)[O:26][C:27]2[CH:28]=[CH:29][C:30]([O:31][CH:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34])=[CH:38][CH:39]=2)[CH:19]=[C:18]([F:20])[C:17]=1[C:21]([F:22])([F:23])[F:24]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterHCID 867487112-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl 3,4-dinitrophenyl ether

Produkt 1

HCID 86748710Methyl 2-{p-{5-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}propionateAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-α,α,α,6-tetrafluoro-p-tolyl 3,4-dinitrophenyl ether (5.0 g, 0.013 mol), methyl 2-(p-hydroxyphenoxy)propionate (5.15 g, 0.026 mol) and potassium carbonate (3.6 g, 0.026 mol) in acetonitrile is refluxed for 18 hours, cooled to room temperature, poured into water and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and methylene chloride gives an oil. A solution of the oil in ether is washed sequentially with saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the title product as a yellow oil (1.6 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Aufarbeitung

  1. temperatureis refluxed for 18 hours
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue
  8. customgives an oil
  9. washA solution of the oil in ether is washed sequentially with saturated sodium hydrogen carbonate solution and water
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7fa458723a9c44beb729c2a05151e604
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424280

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