Water → 1-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

HRID 1894305Notes

Reaction equation

HRID 1894305 reaction equation
[C:1]1([C:8]([O:10]C)=[O:9])([C:4]([O:6][CH3:7])=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+].O>CO>[CH3:7][O:6][C:4]([C:1]1([C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 27695391,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl ester

Product 1

HCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl 1,1-cyclopropanedicarboxylate (5 ml) was mixed with NaOH (1.4 g) in MeOH (40 ml)/water (4 ml). The reaction mixture was stirred at RT overnight and the solvent was evaporated. To the residue was added ether (50 ml), water (50 ml) and extracted once. The aqueous layer was acidified with 6N HCl and extracted three times with ether, the combined organic layer was washed with brine, dried and evaporated to give 1-(methoxycarbonyl)cyclopropanecarboxylic acid (4 g).

Workup

  1. customthe solvent was evaporated
  2. additionTo the residue was added ether (50 ml), water (50 ml)
  3. extractionextracted once
  4. extractionextracted three times with ether
  5. washthe combined organic layer was washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-66f32399116545f69cf5f9fe959351fd
Source dataset
uspto-grants-2013_08
Patent number
US08513283B2

Reaction notes

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