Hydrochloric Acid → 5-Methoxy-3,3-dimethyl-5-oxopentanoic acid

HRID 507098

Reaktionsgleichung

Reaktionsgleichung von HRID 507098
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.[CH3:11][O-:12].[Na+].C(OCC)C.Cl>CO>[CH3:11][O:12][C:7](=[O:9])[CH2:8][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 778133,3-Dimethylglutaric anhydrideHCID 10942334Sodium Methoxide

Produkt 1

HCID 5478975-Methoxy-3,3-dimethyl-5-oxopentanoic acidAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Combine 3,3-dimethylglutaric anhydride (1.00 g, 7.03 mmol) and sodium methoxide (2.5 mL, 14.1 mmol, 30 wt % in methanol) in methanol (20 mL) and heat at reflux for 3 h. Cool the reaction to room temperature and pour into ice water (100 mL). Add diethyl ether (25 mL) and adjust the pH of the mixture to pH=2 with 2 N HCl (10 mL) and separate the layers. Extract the aqueous layer with diethyl ether (25 mL) and combine the organic layers, dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford 3,3-dimethylpentanedioic acid monomethyl ester as a colorless oil (0.827 g, 68%): 1H NMR (CDCl3, 300 MHz) δ 1.14 (s, 6H), 2.46 (s, 2H), 2.48 (s, 2H), 3.67 (s, 3H), 10.9 (br s, 1H); APCI MS (Negative mode) m/z 173 [C8H14O4−H]−.

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. temperatureCool
  3. customthe reaction to room temperature
  4. customseparate the layers
  5. extractionExtract the aqueous layer with diethyl ether (25 mL)
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. customremove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1e44b4ef6d004007be4a10cf508c03ea
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786108B2

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