Réaction #1797495

Équation de réaction

4-methoxyphenol

potassium carbonate

acetonitrile

2-ethylhexyl bromide

→

clear oil

Rendement 80.4%

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

Rendement 80.4%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureat reflux for 4 days
3. 3
   TempératureAfter cooling
4. 4
   Autrethe organic phase was separated
5. 5
   ExtractionThe aqueous layer was extracted with hexane
6. 6
   Lavagethe combined organic layers were washed two times with 1.0 M NaOH and water
7. 7
   SéchageAfter drying over MgSO4
8. 8
   Autrethe solvent was removed under reduced pressure
9. 9
   Autreto give an orange oil
10. 10
    workup.DISTILLATIONThe crude product was distilled under reduced pressure

Mode opératoire

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