Reacción #50162

Ecuación de reacción

4-methoxyphenol

1-bromo-2-ethylhexane

→

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

Rendimiento 43.4%

Disolventes

methanol

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathis mixture was heated
2. 2
   Temperaturato reflux for 30 min
3. 3
   TemperaturaThe mixture was then heated
4. 4
   Temperaturato reflux for 18 hours
5. 5
   OtroThe solvent was removed in vacuo
6. 6
   workup.DISSOLUTIONthe residue dissolved in ether (200 ml)
7. 7
   Lavadowashed with dilute aqueous sodium hydroxide (500 ml ) and water (500 ml )
8. 8
   Secadodried over MgSO4
9. 9
   Concentraciónconcentrated in vacuo again
10. 10
    workup.DISTILLATIONDistillation at 120° C./0.1 mm Hg

Procedimiento

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.

Fuente