p-Toluenesulfonic acid → Cyclohexyl 3-sulfanylpropanoate

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Reaction Steps

Into a 250 ml reaction flask equipped with stirrer, thermometer, reflux condenser and heating mantle are placed 100 grams of cyclohexanol; 26 grams of 3-mercaptopropionic acid and 0.5 grams of paratoluene sulfonic acid. The reaction mass is heated to reflux and refluxed for a period of 11 hours. At the end of the 11 hour period of refluxing, the reaction mass is cooled to room temperature. 200 ml Diethylether are added to the reaction mass. The reaction mass is then washed with two 100 ml volumes of 10% aqueous sodium bicarbonate solution followed by one 100 ml volume of water. The reaction mass is dried over anhydrous sodium sulfate and the solvent is recovered on a Buchi evaporator. The reaction mass is then micro distilled on a micro distillation apparatus yielding the following fractions:

Provenance & Evidence