4-Hydroxybenzaldehyde → 4-(3-Trimethylsilanylpropyloxy)benzaldehyde

HRID 721963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 721963
Cl[CH2:2][CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6].[OH:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:6][Si:5]([CH3:8])([CH3:7])[CH2:4][CH2:3][CH2:2][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 75362(3-Chloropropyl)trimethylsilane

Produkt 1

HCID 218815624-(3-Trimethylsilanylpropyloxy)benzaldehydeAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-Chloropropyltrimethylsilane (33.14 g, 0.22 mol) is added dropwise, over 10 minutes, to a mixture of 4-hydroxybenzaldehyde (24.4 g, 0.2 mol) and of potassium carbonate (30.4 g, 0.22 mol) in 150 ml of dry DMF heated to 120° C. under nitrogen. The reaction mixture is left for 2 hours 30 minutes at 120–130° C. It is cooled and poured into ice-cold water. The aqueous phase is extracted 3 times with dichloromethane. The organic phases are dried over sodium sulfate and concentrated under vacuum. After vacuum distillation (0.2 mmHg), 40.5 g (yield: 86%) of 4-(3-trimethylsilanylpropyloxy)benzaldehyde are obtained in the form of a colorless oil which distils at 110–114° C. and which is used as it is in the next step.

Aufarbeitung

  1. temperatureIt is cooled
  2. additionpoured into ice-cold water
  3. extractionThe aqueous phase is extracted 3 times with dichloromethane
  4. dry with materialThe organic phases are dried over sodium sulfate
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-af52416e7953446c969c43d5163fc15f
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138108B2

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