Vanillin → 3-Methoxy4-(3-trimethylsilanylpropyloxy)benzaldehyde

HRID 427196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427196
Cl[CH2:2][CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6].[O:9]=[CH:10][C:11]1[CH:19]=[CH:18][C:16]([OH:17])=[C:13]([O:14][CH3:15])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][O:14][C:13]1[CH:12]=[C:11]([CH:19]=[CH:18][C:16]=1[O:17][CH2:2][CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6])[CH:10]=[O:9]

Komponenten

5

Edukt 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 75362(3-Chloropropyl)trimethylsilane

Produkt 1

HCID 184631723-Methoxy4-(3-trimethylsilanylpropyloxy)benzaldehydeAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-chloropropyltrimethylsilane (33.14 g, 0.22 mol) was added dropwise over 20 minutes to a mixture of vanillin (30.4 g, 0.2 mol) and potassium carbonate (30.4 g, 0.22 mol) in 150 ml of dry DMF heated to 80° C. under nitrogen. The mixture was maintained for 4 hours at 95°-110° C. The reaction mixture was cooled and poured into ice-cold water. The aqueous phase was extracted three times with dichloromethane. The organic phases were dried over sodium sulfate and concentrated under vacuum. After distillation under vacuum (0.04 mm Hg), 47.5 g (yield: 89%) of 3-methoxy-4-(3-trimethylsilanylpropyloxy) benzaldehyde were obtained in the form of a slightly pinkish oil distilling at 112°-114° C. and employed without further purification in the following step.

Aufarbeitung

  1. temperatureThe mixture was maintained for 4 hours at 95°-110° C
  2. temperatureThe reaction mixture was cooled
  3. additionpoured into ice-cold water
  4. extractionThe aqueous phase was extracted three times with dichloromethane
  5. dry with materialThe organic phases were dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. distillationAfter distillation under vacuum (0.04 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-706f3851e3ca4ff38ca96cc8e02274b9
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06312673B2

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