Potassium Hydroxide → 1-(Ethoxycarbonyl)cyclopropanecarboxylic acid

HRID 1517897Notes

Reaction equation

HRID 1517897 reaction equation
[C:1]1([C:9]([O:11]CC)=[O:10])([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:3][CH2:2]1.[OH-].[K+]>C(O)C.O>[CH2:7]([O:6][C:4]([C:1]1([C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1)=[O:5])[CH3:8]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 73790Diethyl cyclopropane-1,1-dicarboxylate

Product 1

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acidYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of diethyl cyclopropane-1,1-dicarboxylate (4.77 g, 25.6 mmol) in ethanol (40 mL) was added KOH (1.43 g, 25.6 mmol) in H2O (8 mL), and the reaction mixture was stirred at room temperature overnight. The ethanol was removed under reduced pressure. The residue was neutralized with HCl (6 mL, 5 mol/L), then extracted with EtOAc (100 mL×3). The combined organic phases were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (3.58 g, 88.4%).

Workup

  1. customThe ethanol was removed under reduced pressure
  2. extractionextracted with EtOAc (100 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-5d48c9c3f1224b5cbaa0534a8400f772
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

Loading…