Hydrochloric Acid → 3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid

HRID 1992223

Reaction equation

HRID 1992223 reaction equation
[CH3:1][C:2]([CH3:13])([C:8]([O:10]CC)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH-].[K+].CCOC(C)=O.Cl>CCO>[CH2:6]([O:5][C:3](=[O:4])[C:2]([CH3:13])([CH3:1])[C:8]([OH:10])=[O:9])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 15382Diethyl dimethylmalonate

Product 1

HCID 2317543-Ethoxy-2,2-dimethyl-3-oxopropanoic acidYield 77.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl dimethylpropanedioate (10 g, 53 mmol) in 170 mL EtOH was treated with 3.00 g (53 mmol) KOH at ambient temperature for 4 days. The reaction mixture was concentrated to dryness and partitioned between EtOAc and water. The aqueous phase was isolated, combined with fresh EtOAc and the pH adj to 2 with 6N HCl. The organic phase was isolated and the aqueous portion extracted twice with EtOAc. The organic phases were combined, dried over MgSO4, filtered and concentrated to give 6.56 g (41 mmol) 3-(ethyloxy)-2,2-dimethyl-3-oxopropanoic acid as a clear oil. 1H NMR (300 MHz, CDCl3) d 4.20 (q, J=7.1 Hz, 2H), 1.46 (s, 6H), 1.26 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between EtOAc and water
  3. customThe aqueous phase was isolated
  4. customThe organic phase was isolated
  5. extractionthe aqueous portion extracted twice with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-03a893920a5a4ae3bb88bbc83d461570
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Linked notes

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