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Potassium Hydroxide → 1-(Phenylcarbamoyl)cyclopropanecarboxylic acid

HRID 1969423
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1969423
[C:1]1([NH:7][C:8]([C:10]2([C:13]([O:15]CC)=[O:14])[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)C.C1COCC1.O>[C:1]1([NH:7][C:8]([C:10]2([C:13]([OH:15])=[O:14])[CH2:11][CH2:12]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 14150218Ethyl 1-(phenylaminocarbonyl)cyclopropanecarboxylate

Produkt 1

HCID 190968711-(Phenylcarbamoyl)cyclopropanecarboxylic acidAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 1-(phenyl carbamoyl)cyclopropane carboxylate (13 g, 55.79 mmol) in ethanol/THF (1/1, 100 mL) was added KOH (4.69 g, 83.69 mmol) in H2O (8 mL) and the mixture was stirred at room temperature overnight. The ethanol and THF were removed under reduced pressure. The residue was neutralized with HCl (5 mol/L, 20 mL), and extracted with EtOAc (150 mL×3). The combined organic phases were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to afford the title compound as a white solid (10.1 g, 88.6%).

Aufarbeitung

  1. customThe ethanol and THF were removed under reduced pressure
  2. extractionextracted with EtOAc (150 mL×3)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ffef160f8b074b32aec9d1e0a1a4f891
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426585B2

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