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

HRID 1992223

Reaktionsgleichung

Reaktionsgleichung von HRID 1992223
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 2317543-Ethoxy-2,2-dimethyl-3-oxopropanoic acidAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-03a893920a5a4ae3bb88bbc83d461570
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645771B2

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