1-Bromooctane → 4-(Octyloxy)benzonitrile

HRID 1768880Notes

Reaction equation

HRID 1768880 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1O)#[N:2].[C:10](=[O:13])([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]C>CC(=O)CC>[CH2:10]([O:13][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 119072-Hydroxybenzonitrile

Product 1

HCID 1451614-(Octyloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of cyanophenol (25 g) and potassium carbonate (58 g) in 2-butanone (320 ml) was added bromooctane (61 ml) at room temperature. The stirred mixture was heated under reflux for 48 hrs (i.e., until TLC revealed complete reaction). The mixture was filtered, after which the solvent and excess alkyl bromide were removed in vacuo to give a colorless liquid.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 48 hrs
  3. custom(i.e., until TLC revealed complete reaction)
  4. filtrationThe mixture was filtered
  5. customafter which the solvent and excess alkyl bromide were removed in vacuo
  6. customto give a colorless liquid

Sources & evidence

ORD record
ord-a816a39e40f04042bd2757470488c562
Source dataset
uspto-grants-1995_01
Patent number
US05380460

Reaction notes

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