1,6-Dibromohexane → 1-Bromo-6-isopentyloxy hexane

Participants

Reaction Steps

4.8 g (0.11 mol) of 55 % sodium hydride dispersion are added at 20°-40°C over the course of 1 hour, to 74 g (1.0 mol) of isopentyl alcohol. After stirring for 2 hours at 20°-25°C, 24.4 g (0.10 mol) of 1,6-dibromohexane are added dropwise over the course of 15 minutes. The mixture is stirred at 60°C for 16 hours, then filtered and the filtrate is taken up in ether. The ether solution is extracted with saturated sodium chloride slution, dried with sodium sulphate and evaporated at 40°C/18 mm Hg. After chromatography of the residue on silica gel with hexane/ethyl acetate (99:1) and subsequent distillation (B.P. 85°-87°/1 mm), 1-bromo-6-isopentyloxy-hexane is obtained as a slightly yellow clear liquid.

Provenance & Evidence