Sodium Hydroxide → 1-(Ethoxycarbonyl)cyclopropanecarboxylic acid

HRID 1026578Notes

Reaction equation

HRID 1026578 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-].[Na+]>C(O)C>[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 14798Sodium HydroxideHCID 73790Diethyl cyclopropane-1,1-dicarboxylate

Product 1

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acidYield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (93 ml) of diethyl cyclopropane-1,1-dicarboxylate (9.31 g) was added 1 N aqueous sodium hydroxide solution (50 ml), followed by stirring at room temperature for 9 hours. Ethanol was distilled off under reduced pressure, and the remaining aqueous solution was washed with dichloromethane. Under ice cooling, 5 N hydrochloric acid was added to the aqueous layer, and extracted with dichloromethane. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 1-(ethoxycarbonyl)cyclopropanecarboxylic acid (6.38 g).

Workup

  1. distillationEthanol was distilled off under reduced pressure
  2. washthe remaining aqueous solution was washed with dichloromethane
  3. additionUnder ice cooling, 5 N hydrochloric acid was added to the aqueous layer
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a3fd61f1e6547bcb13f4c78337cc57f
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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