4-Bromophenol → Benzene, 1-bromo-4-(hexyloxy)-

HRID 327359Notes

Reaction equation

HRID 327359 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]([O:15][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:11][CH2:10][CH2:9][CH2:14][CH3:13]

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 81011-BromohexaneHCID 11430Potassium Carbonate

Product 1

HCID 520492Benzene, 1-bromo-4-(hexyloxy)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1-bromohexane (60 g) in acetone (150 ml) is added dropwise to a stirred mixture of 4-bromphenol (71 g) and K2CO3 (120 g) in acetone 600 ml) at room temperature. The stirred mixture is heated under reflux for 43 hrs (i.e. until glc revealed complete reaction). The product is extracted into ether twice, and the combined ethereal extracts are washed with water, 5% NaOH water and dried (MgSO4). The solvent is removed in vacuo and the residue was distilled (bp=100°-110° C. at 0.1 mm Hg) to yield a colourless liquid.

Workup

  1. temperatureThe stirred mixture is heated
  2. temperatureunder reflux for 43 hrs
  3. custom(i.e. until glc revealed complete reaction)
  4. extractionThe product is extracted into ether twice
  5. washthe combined ethereal extracts are washed with water, 5% NaOH water
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed in vacuo
  8. distillationthe residue was distilled (bp=100°-110° C. at 0.1 mm Hg)
  9. customto yield a colourless liquid

Sources & evidence

ORD record
ord-98b4d89affbc4552a6f68b6a40eecafe
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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