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Dichloromethane → 4-[(1-Ethoxy)ethoxy]cinnamyl acetoacetate

HRID 2291356
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2291356
ClCCl.[CH2:4]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([CH:14]=[CH:15][CH2:16][OH:17])=[CH:12][CH:11]=1)[CH3:5].[CH2:20]=[C:21]1[O:25][C:23](=[O:24])[CH2:22]1>C([O-])(=O)C.[Na+].CCCCCC>[C:23]([O:17][CH2:16][CH:15]=[CH:14][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][O:6][CH2:4][CH3:5])=[CH:19][CH:18]=1)(=[O:24])[CH2:22][C:21]([CH3:20])=[O:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 12661Diketene2×HCID 545716914-[(1-Ethoxy)ethoxy]cinnamyl alcohol

Produkt 1

HCID 542124814-[(1-Ethoxy)ethoxy]cinnamyl acetoacetateAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 517045Sodium AcetateKatalysator
HCID 8058
Hexane
Lösungsmittel

Versuchsvorschrift

36 Milliliters of dichloromethane was added to 12 g of 4-[(1-ethoxy)ethoxy]cinnamyl alcohol, then 60 mg of anhydrous sodium acetate was added thereto. Under refluxing condition, 5 g of diketene was added dropwise to the reaction mixture, and 2 hours later, 0.42 g diketene was further added thereto, the whole reaction mixture was refluxed for 1.5 hours. After the reaction was completed, the dichloromethane was removed by evaporation under reduced pressure, and the residue thus obtained was stirred for 30 minutes with 27 ml of hexane and 1.2 g of activated carbon. The activated carbon was removed by filtration, and the filtrate was concentrated to obtain 15 g of 4-[(1-ethoxy)ethoxy]cinnamyl acetoacetate as in the form of an oily substance.

Aufarbeitung

  1. additionwas added dropwise to the reaction mixture, and 2 hours later
  2. customthe whole reaction mixture
  3. temperaturewas refluxed for 1.5 hours
  4. customthe dichloromethane was removed by evaporation under reduced pressure
  5. customthe residue thus obtained
  6. customThe activated carbon was removed by filtration
  7. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2b0d5da75c5b4553bbf27d093634e087
Quelldatensatz
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04795814

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