1-Bromooctadecane → 139536-08-6

HRID 2220553Notes

Reaction equation

HRID 2220553 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 59773629139536-08-6

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-71d61926d01c471cbedb848e244cee65
Source dataset
uspto-grants-2008_08
Patent number
US07417154B2

Reaction notes

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