Sodium Hydroxide → 1-(Ethoxycarbonyl)cyclopropanecarboxylic acid

HRID 1436374Notes

Reaction equation

HRID 1436374 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]([C:8]1([C:11]([O:13]CC)=[O:12])[CH2:10][CH2:9]1)=[O:7])[CH3:4]>C(O)C.C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1([C:11]([OH:13])=[O:12])[CH2:9][CH2:10]1)=[O:7])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 73790Diethyl cyclopropane-1,1-dicarboxylate

Product 1

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acidYield 91.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1 N NaOH (275 mL, 275 mmol) was added under nitrogen dropwise to a solution of 1,1-cyclopropanedicarboxylic acid diethyl ester (51.3121 g, 275 mmol) in 400 mL of absolute ethanol at room temperature. After the addition, the reaction was allowed to stir at room temperature overnight. The reaction was concentrated under reduced pressure to remove most of the ethanol. The residue was partitioned between water and ether. The aqueous layer was separated, extracted with ether, acidified with 2 N HCl and extracted four times with ether. The combined extracts were dried (anhydrous MgSO4) and the solvent removed under reduced pressure to give a yellow oil. The oil was dissolved in methylene chloride, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1,1-cyclopropanedicarboxylic acid monoethyl ester (39.8275 g, 91%) as a yellow oil.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customto remove most of the ethanol
  4. customThe residue was partitioned between water and ether
  5. customThe aqueous layer was separated
  6. extractionextracted with ether
  7. extractionextracted four times with ether
  8. dry with materialThe combined extracts were dried (anhydrous MgSO4)
  9. customthe solvent removed under reduced pressure
  10. customto give a yellow oil
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f0c6220bbcad42b5bad9a4ab5c62df2c
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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