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Water → Ethyl 4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate

HRID 1065782
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1065782
[CH2:1]([O:3][C:4](=[O:12])[C:5]([CH3:11])([CH3:10])[C:6](=[O:9])[CH2:7]Br)[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]([CH3:11])([CH3:10])[C:6](=[O:9])[CH2:7][O:20][C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 12822309Ethyl 4-bromo-2,2-dimethyl-3-oxobutanoate

Produkt 1

HCID 53810952Ethyl 4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoateAusbeute 56,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

316 g (2 mol) of 4-bromo-2,2-dimethyl-3-keto-butanoic acid ethyl ester were added dropwise, at 30° C., to 246 g (2 mol) of 4-chlorophenol and 210 g of potassium carbonate in 1,000 ml of dimethylformamide. The mixture was stirred for 20 hours at room temperature and 2 hours at 40° C. The reaction mixture was then introduced into 2,000 ml of water. The aqueous phase was extracted by shaking twice with 500 ml of methylene chloride at a time and the organic phase was extracted by shaking twice with 250 ml of water each time. The combined organic phases were dried, concentrated and distilled. 324 g (56% of theory) of 4-(4-chlorophenoxy)-2,2-dimethyl-3-keto-butanoic acid ethyl ester of melting point 125-135° C./0.1 mm Hg were obtained.

Aufarbeitung

  1. extractionThe aqueous phase was extracted
  2. stirringby shaking twice with 500 ml of methylene chloride at a time
  3. extractionthe organic phase was extracted
  4. stirringby shaking twice with 250 ml of water each time
  5. customThe combined organic phases were dried
  6. concentrationconcentrated
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-c6c7534911b443d39d4843272e860876
Quelldatensatz
uspto-grants-1982_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04331674

Notizen zur Reaktion

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