p-Toluenesulfonic acid → 4,4-Dimethyl-8-bromothiochroman

Participants

Reaction Steps

26.00 g (102.0 mmol) of 2-bromo-1-(3-methylbut-2-enylthio)benzene, 180 ml of toluene and 23.20 g (122.0 mmol) of para-toluenesulphonic acid are introduced into a three-necked flask. The reaction medium is refluxed for four hours and evaporated to dryness. The residue is taken up in aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate, and the organic phase is separated out by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica, eluting with heptane. 20.00 g (76%) of the expected compound are collected in the form of an orange-coloured oil.

Provenance & Evidence