Réaction #5311

Équation de réaction

NaH

2,6-dimethylbenzenethanol

1,6-dibromohexane

H2O

→

title compound

Rendement 52.7%

2-[2-[(6-Bromohexyl)oxy]ethyl]-1,3-dimethylbenzene

Rendement 52.7%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was refluxed for 18 h
2. 2
   ExtractionThe resulting emulsion was extracted with ER (3×100 ml)
3. 3
   Extractionthe dried extract
4. 4
   Autrewas evaporated
5. 5
   Autreto leave a yellow oil
6. 6
   AutreExcess 1,6-dibromohexane was removed under reduced pressure
7. 7
   Autrethe residue was purified on a column of silica (300 ml) [B]

Mode opératoire

NaH (46% dispersion in oil; 4.2 g) was added portionwise to a solution f 2,6-dimethylbenzenethanol (6.0 g) and 1,6-dibromohexane (19.52 g) in THF (50 ml) under nitrogen. The mixture was refluxed for 18 h and treated cautiously with H2O (20 ml). The resulting emulsion was extracted with ER (3×100 ml) and the dried extract was evaporated to leave a yellow oil. Excess 1,6-dibromohexane was removed under reduced pressure and the residue was purified on a column of silica (300 ml) [B] to give the title compound as a colourless oil (6.6 g) b.p. 110-115°/0.4 mmHg.

Source