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

HRID 1665667Notes

Reaction equation

HRID 1665667 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]([C:7]1([C:10]([O:12]C)=[O:11])[CH2:9][CH2:8]1)=[O:6]>CO>[CH3:3][O:4][C:5]([C:7]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 27695391,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl ester

Product 1

HCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acidYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KOH (42 mg, 0.75 mmol) was added to a solution cyclopropane-1,1-dicarboxylic acid dimethyl ester (100 mg, 0.63 mmol) in methanol. The resulting mixture was stirred for 4 hours at ambient temperature then concentrated. The residue was diluted with water, acidified with conc. HCl and the product was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 65 mg (71%) of cyclopropane-1,1-dicarboxylic acid methyl ester.

Workup

  1. concentrationthen concentrated
  2. additionThe residue was diluted with water
  3. extractionthe product was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6273da2160c846a3bd51cf853cf3e0ce
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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