Réaction #5305

Équation de réaction

H2O

NaH

4-phenyl-1-butanol

1,6-dibromohexane

→

title compound

Rendement 48.0%

[4-[(6-Bromohexyl)oxy]butyl]benzene

Rendement 48.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting suspension was refluxed for 27 h
2. 2
   ExtractionThe mixture was extracted with ER (2×200 ml)
3. 3
   Extractionthe dried extract
4. 4
   Autrewas evaporated
5. 5
   Autreto leave an orange oil
6. 6
   AutreThe oil was purified on a column of silica (800 ml) [A]
7. 7
   Autreto give a yellow oil which
8. 8
   workup.DISTILLATIONon distillation

Mode opératoire

NaH (46% dispersion in oil; 6.5 g) was added portionwise to a solution of 4-phenyl-1-butanol (15.0 g) and 1,6-dibromohexane (48.8 g) in THF (200 ml) under nitrogen. The resulting suspension was refluxed for 27 h and treated with H2O (80 ml). The mixture was extracted with ER (2×200 ml) and the dried extract was evaporated to leave an orange oil. The oil was purified on a column of silica (800 ml) [A] to give a yellow oil which on distillation gave the title compound as a colourless oil (15.0 g) b.p. 90-95/0.1 mmHg.

Source