4-Bromophenol → p-Bromophenyl octyl ether

HRID 36817

Reaction equation

HRID 36817 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 145298p-Bromophenyl octyl etherYield 63.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 100 ml of acetone, 8.0 g of 4-bromophenol, 8.9 g of n-octylbromide, and 13 g of potassium carbonate were heated to reflux for 12 hours. After the solvent was distilled off under a reduced pressure, the residue thus obtained was extracted with isopropyl ether, washed with a 5% aqueous sodium hydroxide solution and water in turn. The ether was distilled off, and the residue was purified by a silica gel column chromatography using a mixed solvents of n-hexane and diethyl ether (10:1) and subjected to distillation to obtain 8.4 g of 4-bromo-1-n-octyloxybenzene.

Workup

  1. temperatureto reflux for 12 hours
  2. distillationAfter the solvent was distilled off under a reduced pressure
  3. customthe residue thus obtained
  4. extractionwas extracted with isopropyl ether
  5. washwashed with a 5% aqueous sodium hydroxide solution and water in turn
  6. distillationThe ether was distilled off
  7. customthe residue was purified by a silica gel column chromatography
  8. distillationsubjected to distillation

Sources & evidence

ORD record
ord-1008d93569fe4f328b166d92dc104611
Source dataset
uspto-grants-1995_05
Patent number
US05417885

Linked notes

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