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

Participants

Reaction Conditions

Reaction Steps

36.0 g (0.40 mol) of 1,4-butandiol are added over the course of 20 minutes of a suspension of 12.20 g (0.279 mol) of 55 % sodium hydride in 400 cc of absolute 1,2-dimethoxyethane. The mixture is stirred at 55° C for 2 hours. After this period, 40.2 g (0.266 mol) of isopentyl bromide are added dropwise at 55°, over the course of 20 minutes, and the mixture is then stirred at 60° for 48 hours. The reaction mixture is cooled, filtered and the filtrate is evaporated at 40° /12 mm Hg. The residue is distilled at 0.9 mm Hg and for further purification the fraction, having a B.P. of 75° - 88°/0.09 mm Hg, is taken up in ether and washed with water. 4-Isopentyloxy-1-butanol is obtained as a gas-chromatographically pure oil.

Provenance & Evidence