Sodium Hydroxide → 1-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

HRID 2104370Notes

Reaction equation

HRID 2104370 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]([O:10]C)=[O:9])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27695391,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl ester

Product 1

HCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acidYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Cyclopropanedicarboxylic acid dimethyl ester (25 g) was dissolved in methanol (250 mL). The solution was cooled under ice cooling, and 1N aqueous sodium hydroxide (158 mL) was added dropwise thereto. The thus-obtained mixture was brought back to room temperature, and was stirred overnight. Methanol was distilled away, and the residue was washed with chloroform. The aqueous layer was cooled under ice cooling, and concentrated aqueous HCl was added thereto, to thereby adjust to pH 2. The resultant mixture was extracted with ethyl acetate, and the extract was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, to thereby give the title compound (16.8 g).

Workup

  1. temperatureThe solution was cooled under ice cooling
  2. customwas brought back to room temperature
  3. distillationMethanol was distilled away
  4. washthe residue was washed with chloroform
  5. temperatureThe aqueous layer was cooled under ice cooling
  6. additionconcentrated aqueous HCl was added
  7. extractionThe resultant mixture was extracted with ethyl acetate
  8. dry with materialthe extract was dried over sodium sulfate anhydrate
  9. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-3cc6ce6cf5ae4525bdd34f5aac34fc15
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

Loading…