Hydrochloric Acid → Cyclopropane-1,2,3-tricarboxylic acid

HRID 54709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54709
[CH:1]1([C:12]([O:14]C)=[O:13])[CH:3]([C:4]([O:6]C)=[O:5])[CH:2]1[C:8]([O:10]C)=[O:9].[OH-].[Na+].Cl>CO>[CH:2]1([C:8]([OH:10])=[O:9])[CH:3]([C:4]([OH:6])=[O:5])[CH:1]1[C:12]([OH:14])=[O:13]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12659895Trimethyl cyclopropane-1,2,3-tricarboxylate

Produkt 1

HCID 699248Cyclopropane-1,2,3-tricarboxylic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Trimethyl cyclopropane-1,2,3-tricarboxylate (20.6 g, 95.2 mmols) was dissolved in methanol (200 ml), followed by dropwise adding sodium hydroxide (23.7 g, 593 mmol) (dissolved in water (100 ml)) at room temperature, thereafter heating and reacting the mixture under reflux for one hour, cooling the reaction product, adding conc. hydrochloric acid (40 g, 1.1 mol), concentrating the reaction solution, adding acetone (200 ml) to the concentrated residue, heating the mixture under reflux for 2 hours, filtering off the precipitate, and concentrating the filtrate under reduced pressure, to obtain cyclopropane-1,2,3-tricarboxylic acid (16.0 g, 91.9 mmol, 97%).

Aufarbeitung

  1. temperatureheating
  2. temperatureunder reflux for one hour
  3. temperaturecooling the reaction product
  4. concentrationconcentrating the reaction solution
  5. additionadding acetone (200 ml) to the concentrated residue
  6. temperatureheating the mixture
  7. temperatureunder reflux for 2 hours
  8. filtrationfiltering off the precipitate
  9. concentrationconcentrating the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c5fe50e6123044209265219794a0709b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623078

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