Acetic Acid → 3-(6-Chloro-1-oxo-2,3-dihydro-1H-inden-2-yl)propanoic acid

HRID 326007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 326007
N1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=3)[CH2:8][CH:7]=2)CCCC1.[C:16]([O:20]C)(=[O:19])[CH:17]=[CH2:18].C(O)(=[O:24])C.Cl>O1CCOCC1>[Cl:15][C:12]1[CH:13]=[C:14]2[C:9]([CH2:8][CH:7]([CH2:18][CH2:17][C:16]([OH:20])=[O:19])[C:6]2=[O:24])=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 204636741-(5-Chloro-1H-inden-3-yl)pyrrolidine

Produkt 1

HCID 130516493-(6-Chloro-1-oxo-2,3-dihydro-1H-inden-2-yl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Twenty-two (22) grams of 3-pyrrolidino-5-chloroindene and 18 g of methyl acrylate were dissolved in 70 ml of dioxane, refluxed for 5 hours and freed of the solvent by distilling it off, to obtain a residue. The thus obtained residue was incorporated with 100 ml of acetic acid and 100 ml of hydrochloric acid and heated for 3 hours. After the end of the reaction, the resulting reaction mixture was freed of the solvent by distilling it off under a reduced pressure and incorporated with iced water to precipitate crystals. The crystals so precipitated were filtered off, washed with water, dried and then recrystallized from ethyl acetate to obtain 16 g of 6-chloro-1-oxo-2,3-dihydro-2-indene propionic acid in the colorless needle form.

Aufarbeitung

  1. temperaturerefluxed for 5 hours
  2. distillationby distilling it off,
  3. customto obtain a residue
  4. temperatureheated for 3 hours
  5. customAfter the end of the reaction
  6. customthe resulting reaction mixture
  7. distillationby distilling it off under a reduced pressure
  8. customincorporated with iced water to precipitate crystals
  9. customThe crystals so precipitated
  10. filtrationwere filtered off
  11. washwashed with water
  12. customdried
  13. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3a215ff5476f483d9c6c8d1c47eba8e6
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04443626

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