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

Participants

Reaction Steps

NaH (46% dispersion in oil; 4.2 g) was added portionwise to a solution of 2,6-dimethylbenzeneethanol (6.0 g) and 1,6-dibromohexane (19.52 g) in THP (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 colorless oil (6.6 g) b.p. 110°-115°/0.4 mmHg.

Provenance & Evidence