Hydroxide → 1-(Ethoxycarbonyl)cyclopropanecarboxylic acid

HRID 2352297Notes

Reaction equation

HRID 2352297 reaction equation
[OH-].[C:2]1([C:10]([O:12]CC)=[O:11])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:4][CH2:3]1>O.C(O)C>[CH2:8]([O:7][C:5]([C:2]1([C:10]([OH:12])=[O:11])[CH2:3][CH2:4]1)=[O:6])[CH3:9]

Participants

5

Reactant 2

HCID 961HydroxideHCID 73790Diethyl cyclopropane-1,1-dicarboxylate

Product 1

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of soduim hydroxide (2.15 g, 54 mmol) in water (15 ml) was added dropwise to a stirred solution of diethyl 1,1-cyclopropanedicarboxylate (10 g, 54 mmol) in ethanol (30 ml) while the temperature was maintained below 25° C. After the completion of the addition, the resulting mixture was stirred at room temperature for 60 hours. Most of ethanol was removed by evaporation in vacuo and the residue was diluted with brine, acidified with 6N hydrochloric acid and extracted with diethyl ether. The extract was dried over magnesium sulfate, filtered and concentrated. The residue was purified by distillation to give the title compound (bp 66°-9° C./0.15 mm) as a viscous oil.

Workup

  1. temperaturewas maintained below 25° C
  2. additionAfter the completion of the addition
  3. customMost of ethanol was removed by evaporation in vacuo
  4. additionthe residue was diluted with brine
  5. extractionextracted with diethyl ether
  6. dry with materialThe extract was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-55e421b9c01c4bfd86ff7e5976068c7b
Source dataset
uspto-grants-1989_10
Patent number
US04876279

Reaction notes

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