4-Hydroxybenzaldehyde → 4-Trimethylsilanylmethoxybenzaldehyde

HRID 899016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899016
Cl[CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:4][Si:3]([CH2:2][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 75361Silane, (chloromethyl)trimethyl-

Produkt 1

HCID 565289644-TrimethylsilanylmethoxybenzaldehydeAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Chloromethyltrimethylsilane (110.5 g, 0.9 mol) is added dropwise over 30 minutes to a mixture of para-hydroxybenzaldehyde (110 g, 0.82 mol) and potassium carbonate (124.5 g, 0.9 mol) in 1 L of dry DMF maintained at 80° C., and while sparging with nitrogen. The mixture is left at 90° C. for 4 hours. The reaction mixture is filtered and the solvent is removed from the filtrate by distillation under vacuum. The final traces of DMF are removed via a stage at 60° C. under a vacuum of 2 mmHg. 142.4 g (yield: 84%) of 4-trimethylsilanylmethoxybenzaldehyde are obtained in the form of an orange-yellow oil, which is used without further purification in the next step.

Aufarbeitung

  1. customwhile sparging with nitrogen
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent is removed from the filtrate by distillation under vacuum
  4. customThe final traces of DMF are removed via a stage at 60° C. under a vacuum of 2 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-dfab117446f04b698ae0f92944dbd878
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354571B2

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