Sodium Methoxide → 5-Bromo-2-(7-methoxyheptyloxy)-1,3-dimethylbenzene

HRID 1816726

Reaktionsgleichung

Reaktionsgleichung von HRID 1816726
[Br:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br)=[C:6]([CH3:8])[CH:7]=1.[CH3:19][O-:20].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:20][CH3:19])=[C:6]([CH3:8])[CH:7]=1

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 224946365-Bromo-2-(7-bromoheptyloxy)-1,3-dimethylbenzene

Produkt 1

HCID 224947715-Bromo-2-(7-methoxyheptyloxy)-1,3-dimethylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of crude 5-bromo-2-(7-bromoheptyloxy)-1,3-dimethylbenzene (7.81 g) in methanol (78 ml) was treated with 28% sodium methoxide in methanol (78 ml), and the solution was refluxed for 8 hours. After cooling, the reaction mixture was evaporated under reduced pressure, and the residue was extracted with methylene chloride. The organic layer was dried over magnesium sulfate and magnesium sulfate was filtered off, and then the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with a mixed solvent of n-hexane-ethyl acetate (from 0% to 7% gradient elution) to give 5-bromo-2-(7-methoxyheptyloxy)-1,3-dimethylbenzene (3.34 g) as a colorless oil.

Aufarbeitung

  1. temperaturethe solution was refluxed for 8 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under reduced pressure
  4. extractionthe residue was extracted with methylene chloride
  5. dry with materialThe organic layer was dried over magnesium sulfate and magnesium sulfate
  6. filtrationwas filtered off
  7. customthe filtrate was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a mixed solvent of n-hexane-ethyl acetate (from 0% to 7% gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-f2cfa733b5be49458a48c3a789d932ac
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884868B1

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