1,6-Dibromohexane → 1-[4-[(6-Bromohexyl)oxy]butyl]benzene

Participants

Reaction Steps

To a mixture of 5 ml (32.75 mmol) 4-phenylbutanol with 10.1 ml (65.66 mmol) 1,6-dibromohexane is added 8 g (121.2 mmol) powdered KOH and 1.112 g (3.28 mmol) tetrabutylammonium hydrogen sulfate. After allowing the suspension to stir for 20 hr at room temperature, it is filtered and the filtrate dissolved in 50 ml Et2O. The resulting solution is washed with water, dried on anhydrous Na2SO4, the Et2O evaporated and the residue distilled in vacuum (0.1 mmHg), a first fraction up to 100° C. of a mixture of starting products and a second fraction at 150° C. of 4-(6-bromohexyloxy)butylbenzene weighing 7.60 g (74.4 %) being collected.

Provenance & Evidence