2-Mercaptoethanol → 2-Piperonylthioethanol

Participants

Reaction Steps

0.96 g (0.02 mol) of 50% sodium hydride dispersion are freed from the mineral oil with absolute tetrahydrofuran and suspended in 30 cc of tetrahydrofuran. A solution of 1.56 g (0.02 mol) of 2-mercaptoethanol in 10 cc of tetrahydrofuran is added at 20°-25° while stirring, to this suspension. The mixture is stirred at 60° over the course of 10 hours. After this period a solution of 4.3 g (0.02 mol) of piperonyl bromide in 30 cc of tetrahydrofuran is added dropwise to the mixture. The reaction mixture is stirred at 60° over the course of 8 hours, subsequently cooled to 20° and 100 cc amounts of ether and water are added. The organic phase is separated off in a separating funnel, extracted with saturated sodium chloride solution, dried over sodium sulphate and evaporated. The residue may be purified by chromatography on silica gel with hexane/ethyl acetate (1:2). 2-Piperonylthio-ethanol is obtained as a colourless oil, which according to gas-chromatography is pure.

Provenance & Evidence