Pentanoic acid, 5-[(9-oxo-9H-xanthen-2-yl)oxy]-, ethyl ester → 5-(9-oxo-9H-xanthen-2-yloxy)pentanoic acid

HRID 1197193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197193
[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2>C1C=CC=CC=1.CCO.O.[OH-].[K+]>[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Komponenten

6

Edukt 1

HCID 2818242Pentanoic acid, 5-[(9-oxo-9H-xanthen-2-yl)oxy]-, ethyl ester

Produkt 1

HCID 28182415-(9-oxo-9H-xanthen-2-yloxy)pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 241BenzeneLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

Ethyl 5-(9-oxoxanthen-2-oxy)valerate (8.0 g, 24 mmol) prepared as described above was dissolved in a mixture of benzene (10 mL), 95% EtOH (40 mL), and water (5 mL), and 4N aqueous KOH (8 mL) was added. The mixture was refluxed for 6 hours (reaction complete by TLC), and partially concentrated (final volume ~10 mL). Absolute EtOH (10 mL) was added, and the resulting white precipitate was collected and washed with EtOH (2×10 mL). Yield: 1.7 g (21%), of potassium salt. The filtrate was evaporated, and the residue was dissolved in water (100 mL). The aqueous solution was extracted with EtOAc (3×20 mL), and the aqueous phase was added dropwise to a mixture of ice-water (100 mL) and 12N aqueous HCl (15 mL). A light-gray precipitate formed, which was collected, washed with water (3×10 mL), and dried. Yield: 5.45 g (74%) of free acid. A small amount of the product was recrystallized from n-hexane-EtOH (10:1) for elemental analysis. Fine white needles.

Aufarbeitung

  1. additionwas added
  2. temperatureThe mixture was refluxed for 6 hours
  3. custom(reaction complete by TLC)
  4. concentrationpartially concentrated (final volume ~10 mL)
  5. additionAbsolute EtOH (10 mL) was added
  6. customthe resulting white precipitate was collected
  7. washwashed with EtOH (2×10 mL)
  8. customThe filtrate was evaporated
  9. dissolutionthe residue was dissolved in water (100 mL)
  10. extractionThe aqueous solution was extracted with EtOAc (3×20 mL)
  11. additionthe aqueous phase was added dropwise to a mixture of ice-water (100 mL) and 12N aqueous HCl (15 mL)
  12. customA light-gray precipitate formed
  13. customwhich was collected
  14. washwashed with water (3×10 mL)
  15. customdried
  16. customA small amount of the product was recrystallized from n-hexane-EtOH (10:1) for elemental analysis

Quellen und Nachweise

ORD-Eintrag
ord-ade4b4cff7394986bf6893736b29648f
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05117009

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