Potassium Hydroxide → 1-(Phenylcarbamoyl)cyclopropanecarboxylic acid

HRID 1969423Notes

Reaction equation

HRID 1969423 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-ffef160f8b074b32aec9d1e0a1a4f891
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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