Methanol → Methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate

HRID 436880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436880
S(=O)(=O)(O)O.[CH3:6][C:7]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:8][CH2:9][CH2:10][C:11](=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].[CH3:24][OH:25]>O>[CH3:24][O:25][C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:7]([CH3:6])=[CH:8][CH2:9][CH2:10][C:11](=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 53708905Methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate

Produkt 1

HCID 54124623Methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The product can be obtained in the form of a mixture of E and Z isomers by adding dropwise 3 ml of concentrated sulfuric acid to a solution of 7.6 g of the product of Example 3 in 45 ml of methanol and stirring the mixture at room temperature for 40 hours. The mixture was diluted with water and extracted with methylene chloride. The extracts were washed with water, dried over sodium sulfate and evaporated to dryness and the residue was chromatographed over silica and was eluted with a 9-1 benzene-ethyl acetate mixture to obtain 1.3 g of methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate in the form of a colorless oil.

Aufarbeitung

  1. customThe product can be obtained in the form of a mixture of E and Z isomers
  2. extractionextracted with methylene chloride
  3. washThe extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customthe residue was chromatographed over silica
  7. washwas eluted with a 9-1 benzene-ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-d35d695c5bf94e7da610d4125c65cffd
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04028386

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