Lithium hydroxide, monohydrate → 1-(Phenylcarbamoyl)cyclopropanecarboxylic acid

HRID 476366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 476366
[C:1]1([NH:7][C:8]([C:10]2([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>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

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 66605339Methyl 1-(phenylcarbamoyl)cyclopropanecarboxylate

Produkt 1

HCID 190968711-(Phenylcarbamoyl)cyclopropanecarboxylic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 1-(phenylcarbamoyl)cyclopropanecarboxylate (0.607 g, 2.77 mmol) was dissolved in a mixture of THF (3.5 mL) and water (3.50 mL), lithium hydroxide monohydrate (0.349 g, 8.31 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The THF was removed under reduced pressure and additional water (20 mL) was added. The solution was acidified to ˜pH 4 with 2 M HCl and the off white solid that precipitated was collected by suction filtration and washed with additional water to give 1-(phenylcarbamoyl)cyclopropanecarboxylic acid (0.482 g, 85% yield). MS (ESI) m/z: 206.0 (M+H+)

Aufarbeitung

  1. additionwas added
  2. customThe THF was removed under reduced pressure and additional water (20 mL)
  3. additionwas added
  4. customthe off white solid that precipitated
  5. filtrationwas collected by suction filtration
  6. washwashed with additional water

Quellen und Nachweise

ORD-Eintrag
ord-9f4855de4ee6436b908f900da7b01e6d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637672B2

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