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1-Propanol → Propyl 5-acetylsalicylate

HRID 228628
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228628
[C:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.CN(C)[CH2:17][CH2:18][CH2:19]N=C=N.O.ON1C2C=CC=CC=2N=N1.C(O)CC>CN(C)C=O.O>[C:1]([C:4]1[CH:12]=[C:8]([C:9]([O:11][CH2:17][CH2:18][CH3:19])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10311-PropanolHCID 831515-Acetylsalicylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

Produkt 1

HCID 23078328Propyl 5-acetylsalicylateAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Acetylsalicylic acid (360 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (458 mg), 1-hydroxybenzotriazole hydrate (36.7 mg), and propanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give propyl 5-acetylsalicylate (202 mg, yield 45%).

Aufarbeitung

  1. customto prepare a solution which
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fad00d748a0646eaa0a77af6bd0d9e49
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

Notizen zur Reaktion

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