4-Methoxyphenol → 1-((2-Ethylhexyl)oxy)-4-methoxybenzene

HRID 1721703Notes

Reaction equation

HRID 1721703 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 90154-MethoxyphenolHCID 868042-Ethylhexyl bromide

Product 1

HCID 33410051-((2-Ethylhexyl)oxy)-4-methoxybenzeneYield 43.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium metal (6.50 g, 283 mmol) was dissolved in dry methanol (100 ml) under Ar to give a 2.5M solution of sodium methoxide. A solution of 4-methoxyphenol (29.3 g, 236 mmol) in dry methanol (150 ml) was added and this mixture was heated to reflux for 30 min. After cooling to room temperature, a solution of 1-bromo-2-ethylhexane (46.5 g, 259 mmol) in dry methanol (150 ml) was added dropwise. The mixture was then heated to reflux for 18 hours. The solvent was removed in vacuo, the residue dissolved in ether (200 ml), washed with dilute aqueous sodium hydroxide (500 ml) and water (500 ml), dried over MgSO4 and concentrated in vacuo again. Distillation at 120° C./0.1 mm Hg afforded 24.2 g (43%) 1-methoxy-4-(2'-ethylhexyloxy)benzene.

Workup

  1. temperaturethis mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 18 hours
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in ether (200 ml)
  7. washwashed with dilute aqueous sodium hydroxide (500 ml) and water (500 ml)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo again
  10. distillationDistillation at 120° C./0.1 mm Hg

Sources & evidence

ORD record
ord-6d072dc6ea1340ddb029b38ea036e96e
Source dataset
uspto-grants-1996_04
Patent number
US05512654

Reaction notes

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