1-Bromo-3-methylbutane → 4-Isopentyloxy butanol

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Reaction Steps

To 12.2 g (0.279 mol) of 55% sodium hydride dispersion in oil, suspended in 400 cc of absolute 1,2-dimethoxy ethane, there is added dropwise, under nitrogen, over the course of 20 minutes and while stirring, 360 g (0.40 mol) of 1,4-butandiol in 50 cc of absolute 1,2-dimethoxy ethane. The mixture is stirred at 60° C. for 3 hours, 40.2 g (0.266 mol) of isopentyl bromide are then added and the mixture is stirred at 60° for 22 hours. The resulting sodium bromide is suction filtered, washed with ether and the filtrate is evaporated. For the removal of the excess 1,4-butandiol the residue is taken up in ether, washed three times with water, dried over sodium sulphate and evaporated. After the fractional distillation of the product, pure 4-isopentyloxy butanol, having a B.P. of 80°-81°/0.6 mm Hg, is obtained.

Provenance & Evidence