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4-Chlorophenol → HCID 19979379, Verbindung

HRID 1461763
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1461763
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[N:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[C:19]([N+:25]([O-:27])=[O:26])=[C:18]([CH:28]([CH3:30])[CH3:29])[CH:17]=1.[Cl-].[Na+]>CS(C)=O.C1(C)C=CC=CC=1.O>[CH:22]([C:20]1[C:19]([N+:25]([O-:27])=[O:26])=[C:18]([CH:28]([CH3:30])[CH3:29])[CH:17]=[C:16]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:21]=1)([CH3:24])[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 46844-ChlorophenolHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 19979377HCID 19979377, Verbindung

Produkt 1

HCID 19979379HCID 19979379, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl Sulfoxide
Lösungsmittel
2×
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

0.77 g of 4-chlorophenol and 1.00 g of potassium carbonate are suspended in 6 ml of dimethyl sulfoxide and the suspension is heated for 1 hour at +60° C.; a solution of 1.46 g of 6-chloro-2,4-diisopropyl-3-nitropyridine in 4 ml of dimethyl sulfoxide is then added dropwise. When the addition is complete, the mixture is heated for 1 hour at +120° C. with vigorous stirring. After cooling, the reaction mixture is poured onto 100 ml of water and 50 ml of toluene and then saturated with sodium chloride. The resulting suspension is filtered over diatomaceous earth and the filtrate is extracted with toluene. The organic phase is dried over magnesium sulfate and the solvent is evaporated. The residue is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:30). 2,4-Diisopropyl-6-(4-chlorophenoxy)-3-nitropyridine is obtained in the form of a light-yellow crystalline powder, m.p. 102°-104° C.

Aufarbeitung

  1. temperaturethe suspension is heated for 1 hour at +60° C.
  2. additionWhen the addition
  3. temperaturethe mixture is heated for 1 hour at +120° C. with vigorous stirring
  4. temperatureAfter cooling
  5. filtrationThe resulting suspension is filtered over diatomaceous earth
  6. extractionthe filtrate is extracted with toluene
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. customthe solvent is evaporated
  9. customThe residue is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:30)

Quellen und Nachweise

ORD-Eintrag
ord-ca3fe4f00e26488f81eae6f297fa5b07
Quelldatensatz
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05077304

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