Allyl bromide → 2-Benzyloxy-5-[(2-propenyl)oxy]benzaldehyde

HRID 412166

Reaktionsgleichung

Reaktionsgleichung von HRID 412166
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[CH:25]=[CH2:26].CCOC(C)=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH2:26][CH:25]=[CH2:24])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 185361922-(Benzyloxy)-5-hydroxybenzaldehyde

Produkt 1

HCID 185361832-Benzyloxy-5-[(2-propenyl)oxy]benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of the product from Step A (75.4 mmol) in 100 mL of DMF was added potassium carbonate (20.8 g, 150.7 mmol), followed by allyl bromide (11.7 mL, 135 mmol). The reaction was warmed to 60° C. and stirred for one hour. The solution was poured into EtOAc and washed with water, saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (20-30% EtOAc/hexane) to provide the titled product, along with unreacted starting material (4.39 g, 26%).

Aufarbeitung

  1. washwashed with water, saturated NaHCO3 solution and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting product was purified by silica gel chromatography (20-30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1b40a4cf657d453cb3e06a20ba23ab57
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562823B1

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