Potassium Hydroxide → 1-(Phenylcarbamoyl)cyclopropanecarboxylic acid

HRID 2068218Notes

Reaction equation

HRID 2068218 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 190968711-(Phenylcarbamoyl)cyclopropanecarboxylic acidYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-14460c350415496fa3fdce64a3c4a1cc
Source dataset
uspto-grants-2012_10
Patent number
US08293897B2

Reaction notes

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