Potassium Hydroxide → 3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid

HRID 924624

Reaction equation

HRID 924624 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]([CH3:12])([CH3:11])[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[K+]>C(O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]([CH3:12])([CH3:11])[C:6]([OH:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 15382Diethyl dimethylmalonate

Product 1

HCID 2317543-Ethoxy-2,2-dimethyl-3-oxopropanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25 g 2,2-Dimethyl-malonic acid diethyl ester, 7.8 g potassium hydroxide and 500 ml ethanol were mixed in a round-bottomed flask and refluxed for 3 hours. Then again 2.2 g potassium hydroxide were added and the mixture was refluxed overnight. The solvent was removed on a rotovap, 250 ml H2O were added and the mixture was washed with ether. The aqueous phase was acidified with HCl to pH 3-4 followed by two extractions with dichloromethane. The organic solvent was dried and evaporated and the resulting product was characterized by 1H-NMR.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturethe mixture was refluxed overnight
  3. customThe solvent was removed on a rotovap, 250 ml H2O
  4. additionwere added
  5. washthe mixture was washed with ether
  6. extractionfollowed by two extractions with dichloromethane
  7. customThe organic solvent was dried
  8. customevaporated

Sources & evidence

ORD record
ord-d05ddce2c4654619837edad593ea50d2
Source dataset
uspto-grants-2016_03
Patent number
US09283186B2

Linked notes

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