Réaction #5313

Équation de réaction

4-Methoxybenzeneethanol

1,6-dibromohexane

NaOH

→

oil

1-[2-[(6-Bromohexyl)oxy]ethyl]-4-methoxybenzene

Solvants

H2O

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ER (3×150 ml)
2. 2
   Lavagethe combined organic extracts were washed consecutively with H2O (125 ml), BR (125 ml)
3. 3
   Autredried
4. 4
   Autreevaporated

Mode opératoire

4-Methoxybenzeneethanol (5.0 g) and 1,6-dibromohexane (23.7 g) were stirred rapidly at RT with tetra-n-butyl ammonium bisulphate (0.94 g) and 12.5 M aqueous NaOH (30 ml) for 16 h. The mixture was diluted with H2O (125 ml), extracted with ER (3×150 ml) and the combined organic extracts were washed consecutively with H2O (125 ml), BR (125 ml), dried and evaporated to give an oil (24.6 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.30 g). T.l.c. (CX-ER (40:1)) Rf 0.33.

Source