4-Bromophenol → 1-Bromo-4-[(2-ethylhexyl)oxy]benzene

HRID 2294676Notes

Reaction equation

HRID 2294676 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:12][CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15]>COCCO>[CH2:14]([CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:15]

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromide

Product 1

HCID 225907671-Bromo-4-[(2-ethylhexyl)oxy]benzeneYield 84%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

86.5 g (0.5 mol) of 4-bromophenol in 500 ml of Methylcellosolve are placed in a 1 l sulfonating flask fitted with stirrer, condenser, dropping funnel and internal thermometer. This mixture is heated to 60 C., and then 70.0 g of 30% NaOH (0.53 mol) are run in slowly. The mixture is stirred for 15 minutes and then 116.8 g (0.575 mol) of 3-bromomethylheptane are added dropwise over the course of 45 minutes. The reaction is continued at 100 C. overnight. The thin-layer chromatogram indicates virtually quantitative conversion. Solvent and excess bromide are removed in vacuo and the residue (an oil) is taken up in 600 ml of toluene. The mixture is subjected three times to extraction by shaking with water and the extracts are dried over sodium sulfate and evaporated to dryness, to give 119.3 g (84% of theory) of 4-(2-ethylhexyloxy)bromobenzene as a light yellow oil.

Workup

  1. customfitted with stirrer, condenser
  2. temperatureThis mixture is heated to 60 C
  3. customovernight
  4. customSolvent and excess bromide are removed in vacuo
  5. extractionto extraction
  6. stirringby shaking with water
  7. dry with materialthe extracts are dried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5b3f62d85d9a42b1ae77b7b45f6484d0
Source dataset
uspto-grants-1997_11
Patent number
US05688995

Reaction notes

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