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Potassium Hydroxide → (1R,2S)-2-methoxycarbonylcyclopropane-1-carboxylic acid

HRID 498114
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 498114
[C@@H:1]1([C:8]([O:10]C)=[O:9])[CH2:3][C@@H:2]1[C:4]([O:6][CH3:7])=[O:5].[OH-].[K+]>CO>[CH3:7][O:6][C:4]([C@H:2]1[CH2:3][C@H:1]1[C:8]([OH:10])=[O:9])=[O:5]
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Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 642979Dimethyl (1R,2S)-cyclopropane-1,2-dicarboxylate

Produkt 1

HCID 12510973(1R,2S)-2-methoxycarbonylcyclopropane-1-carboxylic acidAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 150 ml of a methanol solution of 14.68 g (92.8 mmol) of dimethyl cis-1,2-cyclopropanedicarboxylate was added 67 ml of an aqueous solution of 7.52 g (113.9 mmol) of potassium hydroxide under cooling with ice, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure, and to the residue was added water. The reaction mixture was washed with diethyl ether. The aqueous layer was adjusted to pH 2 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 12.38 g (92.5%) of the title compound as a colorless oily substance.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. customthe solvent was removed by evaporation under reduced pressure
  4. additionto the residue was added water
  5. washThe reaction mixture was washed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8ca7fa0ed9a412fae5f876e19778033
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06949662B2

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