Potassium Carbonate → 2-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde

HRID 30094

Reaktionsgleichung

Reaktionsgleichung von HRID 30094
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].[CH2:12](Br)/[CH:13]=[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15]/[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:13]\[CH2:12][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Produkt 1

HCID 597893412-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-hydroxy-6-methoxybenzaldehyde (4.72 g, 30.43 mmol) in dry DMF (50 ml) was added geranyl bromide (7.5 g, 33.50 mmol) followed by solid potassium carbonate (5.5 g, 39.86 mmol). The mixture was stirred at room temperature for 48 h. The suspension was filtered through a layer of dry sodium sulfate (top) and silica gel (bottom), washed with 200 ml ethyl acetate and decanted into a separatory funnel. The mixture was washed sequentially with aqueous ammonium chloride, water (twice), brine, and the organic phase was dried over Na2SO4. The solution was concentrated in vacuo on a rotovap. The brown gel material was then purified by chromatography via silica gel using 8:2 hexanes:ethyl acetate eluent to provide 2-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde as pale yellow oil.

Aufarbeitung

  1. filtrationThe suspension was filtered through a layer of dry sodium sulfate (top) and silica gel (bottom)
  2. washwashed with 200 ml ethyl acetate
  3. customdecanted into a separatory funnel
  4. washThe mixture was washed sequentially with aqueous ammonium chloride, water (twice), brine
  5. dry with materialthe organic phase was dried over Na2SO4
  6. concentrationThe solution was concentrated in vacuo on a rotovap
  7. customThe brown gel material was then purified by chromatography via silica gel using 8:2 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-888504b2d96044d1a3f5147db57b2942
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423045B2

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