4-Hydroxybenzaldehyde → 4-(2-(Diethylamino)-Ethoxy)-Benzaldehyde

HRID 215753

Reaktionsgleichung

Reaktionsgleichung von HRID 215753
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14]Cl)[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([N:12]([CH2:16][CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:13][CH3:14])[CH3:11]

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chloride

Produkt 1

HCID 4116744-(2-(Diethylamino)-Ethoxy)-BenzaldehydeAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To the solution of 18.4 g (0.15 mol) of 4-hydroxybenzaldehyde in 100 ml acetone, 27.5 g (0.16 mol) of N,N-diethyl-N-(2-chlorethyl)-amine IX and 22.1 g (0.16 mol) potassium carbonate was added at the room temperature under stirring. The mixture was then intensively stirred at the boiling temperature for 12 hours. The mixture was cooled, potassium chloride was separated, washed with acetone. The solvent was distilled off from the solution on the vacuum rotatory evaporator. Afforded 20 g (60.6%) of 4-diethylaminoethoxybenzaldehyde X. Colourless fluid boiling point 120-123° C./0.5 torr, n20D=1.536. Lit. [5] reports boiling point 123-125° C./0.8 torr, n20D=1.530.

Aufarbeitung

  1. stirringThe mixture was then intensively stirred at the boiling temperature for 12 hours
  2. temperatureThe mixture was cooled
  3. custompotassium chloride was separated
  4. washwashed with acetone
  5. distillationThe solvent was distilled off from the solution on the vacuum rotatory evaporator

Quellen und Nachweise

ORD-Eintrag
ord-c5d24567c5a94a148b23841095e5169f
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193184B2

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