Acetone → Ethyl 4-(2,4-nonadiynyloxy)-benzoate

HRID 2639

Reaktionsgleichung

Reaktionsgleichung von HRID 2639
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]([CH3:22])=O>CCCCCC.C(OCC)(=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)[C:20]#[C:22][C:12]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 8434EthylparabenHCID 11430Potassium Carbonate

Produkt 1

HCID 18935880Ethyl 4-(2,4-nonadiynyloxy)-benzoateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

In a flask were placed 3.78 g (0.024 mole) of 1-chloro-2,4-nonadiyne thus obtained, 3.32 g (0.02 mole) of ethyl 4-hydroxybenzoate, 5.5 g (0.04 mole) of potassium carbonate, and 50 ml of acetone and the mixture was refluxed by heating for 11 hours. After allowing to cool the reaction mixture to room temperature, the reaction mixture was poured in 250 ml of ice-water and the product was extracted with methylene chloride. After distilling off the solvent of the organic layer, the residue formed was purified by a silica gel column chromatography(developing solvent: hexane/ethyl acetate=3/1) to provide 4.0 g (yield 70%) of ethyl 4-(2,4-nonadiynyloxy)-benzoate.

Aufarbeitung

  1. temperatureby heating for 11 hours
  2. extractionthe product was extracted with methylene chloride
  3. distillationAfter distilling off the solvent of the organic layer
  4. customthe residue formed
  5. customwas purified by a silica gel column chromatography(developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-e5b29654fa7b4c0a9addc6161d045c21
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05730903

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