Hydrochloric Acid → 2-(4-((2-Oxocyclopentylidene)methyl)phenyl)propanoic acid

HRID 652831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 652831
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=O.[O:14]1CCN(C2CCCC=2)CC1.Cl.[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=CC=1>>[O:14]=[C:26]1[CH2:31][CH2:30][CH2:29][C:32]1=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 702941-MorpholinocyclopenteneHCID 102196632-(4-Formylphenyl)propionic acid

Produkt 1

HCID 540467252-(4-((2-Oxocyclopentylidene)methyl)phenyl)propanoic acidAusbeute 82,3 %

Versuchsvorschrift

A solution of 3.56 g (0.02 mole) of 2-(p-formylphenyl)propionic acid and 6.4 g (0.04 mole) of 1-morpholinocyclopentene in 40 ml of toluene was stirred at 60° C. for 3 hours. The mixture was cooled, and 20 ml of 6N hydrochloric acid were then added to the cooled solution, after which the mixture was stirred at room temperature for a further 1 hour. The reaction mixture was then extracted with diethyl ether; the extract was washed with water and dried; and the solvent was removed by evaporation under reduced pressure to afford a crystalline substance, which was recrystallized from a mixture of diethyl ether and hexane, to give 4.0 g (yield 82.3%) of the title compound as white crystals melting at 106°-107° C.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionThe reaction mixture was then extracted with diethyl ether
  3. washthe extract was washed with water
  4. customdried
  5. customand the solvent was removed by evaporation under reduced pressure
  6. customto afford a crystalline substance, which
  7. customwas recrystallized from a mixture of diethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-14a003d7c844402197960a71295b126a
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04673761

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