Reaction #1797495

Reaction equation

4-methoxyphenol

potassium carbonate

acetonitrile

2-ethylhexyl bromide

→

clear oil

Yield 80.4%

1-methoxy-4-(2-ethylhexyloxy)benzene

Yield 80.4%

Solvents

water

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux for 4 days
3. 3
   TemperatureAfter cooling
4. 4
   Otherthe organic phase was separated
5. 5
   ExtractionThe aqueous layer was extracted with hexane
6. 6
   Washthe combined organic layers were washed two times with 1.0 M NaOH and water
7. 7
   DryingAfter drying over MgSO4
8. 8
   Otherthe solvent was removed under reduced pressure
9. 9
   Otherto give an orange oil
10. 10
    workup.DISTILLATIONThe crude product was distilled under reduced pressure

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).

Source