Hydrochloric Acid → p-Bromophenyl octyl ether

HRID 1769564Notes

Reaction equation

HRID 1769564 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([Br:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(=O)CC>[CH2:1]([O:16][C:15]1[CH:14]=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 145298p-Bromophenyl octyl etherYield 66.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A reaction vessel was charged with 22.3 g of octyl bromide, 20 g of p-bromophenol, 33.3 g of potassium carbonate and 200 ml of 2-butanone (MEK), and the mixture was reacted under reflux and agitation for 10 hours. The reaction liquid was poured into diluted hydrochloric acid and the mixture was extracted with benzene. The extract was washed with an aqueous solution of edible salt and dried over Glauber's salt. The solvents were distilled off and the residue was distilled under reduced pressure to obtain 22.0 g (66.8%) of 4-octyloxybromobenzene.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux
  3. customThe reaction liquid
  4. extractionthe mixture was extracted with benzene
  5. washThe extract was washed with an aqueous solution of edible salt
  6. dry with materialdried over Glauber's salt
  7. distillationThe solvents were distilled off
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-58d91f4b281f4ad5acee15c4f72d7117
Source dataset
uspto-grants-1995_01
Patent number
US05382380

Reaction notes

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