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

HRID 915379Notes

Reaction equation

HRID 915379 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22]Br)[CH3:20]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:22][CH:21]([CH2:19][CH3:20])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide

Product 1

HCID 33410051-((2-Ethylhexyl)oxy)-4-methoxybenzeneYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-methoxyphenol (100.0 g, 0.8 mol), dry potassium carbonate (166.7 g, 1.2 mol), acetonitrile (800 mL), and 2-ethylhexyl bromide (173.8 g, 0.9 mol) was stirred mechanically and heated at reflux for 4 days. After cooling, the mixture was diluted with water (1.5 L), and then the organic phase was separated. The aqueous layer was extracted with hexane, and the combined organic layers were washed two times with 1.0 M NaOH and water. After drying over MgSO4, the solvent was removed under reduced pressure to give an orange oil. The crude product was distilled under reduced pressure to give 152 g (80%) of a clear oil. (bp 135-138° C. at 0.4 mmHg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 days
  3. temperatureAfter cooling
  4. customthe organic phase was separated
  5. extractionThe aqueous layer was extracted with hexane
  6. washthe combined organic layers were washed two times with 1.0 M NaOH and water
  7. dry with materialAfter drying over MgSO4
  8. customthe solvent was removed under reduced pressure
  9. customto give an orange oil
  10. distillationThe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-f229099e0e19433dabb9967a7ce38c6d
Source dataset
uspto-grants-2007_09
Patent number
US07265161B2

Reaction notes

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