Ethanol → 1-(Ethoxycarbonyl)cyclopropanecarboxylic acid

HRID 1820612Notes

Reaction equation

HRID 1820612 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.C(O)C>[OH-].[Na+]>[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

4

Reactant 2

HCID 702EthanolHCID 73790Diethyl cyclopropane-1,1-dicarboxylate

Product 1

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Diethyl 1,1-cyclopropane dicarboxylate (20 g) was hydrolyzed in 1N NaOH (107 ml) and ethanol (220 ml) for 16 hours, and the ethanol was removed by distillation under reduced pressure. The remaining starting material was removed by using ethyl acetate and the aqueous layer was acidified by 1N HCl. The reaction mixture was extracted with ethyl acetate and distilled under reduced pressure. The residue was purified by silica gel column to give the title compound in a yield of 94%.

Workup

  1. customthe ethanol was removed by distillation under reduced pressure
  2. customwas removed
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. distillationdistilled under reduced pressure
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-a09a4639369140deb299e1ea2ffdcdc7
Source dataset
uspto-grants-2009_10
Patent number
US07605147B2

Reaction notes

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