1-Bromooctadecane → 4-(Octadecyloxy)-benzonitrile

HRID 507824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507824
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[CH2:28]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Komponenten

6

Edukt 4

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 13387N-methyl-2-pyrrolidone

Produkt 1

HCID 597736294-(Octadecyloxy)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a 750 ml sulfonating flask, 30.0 g (0.252 mol) of 4-hydroxybenzonitrile, 84.0 g (0.252 mol) of 1-bromooctadecane and 48.7 g (0.353 mol) of finely ground potassium carbonate are introduced into 200 ml of N-methylpyrrolidone (NMP) under a nitrogen atmosphere and heated at 120° C., with stirring. After being stirred for 15 hours, the mixture is cooled to room temperature and poured into 2 liters of water, whereupon a light-beige solid precipitates out, which is filtered off and washed with water. After drying at 60° C. and 150 mbar, there are obtained 90.8 g (97% of theory) of a colourless crystalline solid of formula

Aufarbeitung

  1. stirringAfter being stirred for 15 hours
  2. temperaturethe mixture is cooled to room temperature
  3. customprecipitates out, which
  4. filtrationis filtered off
  5. washwashed with water
  6. customAfter drying at 60° C.
  7. custom150 mbar, there are obtained 90.8 g (97% of theory) of a colourless crystalline solid of formula

Quellen und Nachweise

ORD-Eintrag
ord-4b442b7846bb41e8aa52f24f97d86824
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786313B2

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