p-Toluenesulfonic acid → 4-Methyl-2-[2-(methylsulfanyl)ethyl]-1,3-dioxane

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Reaction Steps

Into a 100 ml reaction flask equipped with spin bar, reflux condenser, heating mantle and hot plate with magnetic stirring apparatus is placed 0.2 grams para-toluenesulfonic acid, 5 ml cyclohexane and 4.5 grams of 1,3-butanediol. Slowly added to the reaction mass over a period of 30 minutes is 3-methylthiopropionaldehyde (5.2 grams; 0.05 moles). The reaction mass is then heated to reflux and refluxed for a period of 9 hours. During the refluxing process, water of reaction is removed from the reaction mass. At the end of the 9 hour refluxing period, the reaction mass is then cooled and transferred to a separatory funnel and washed with one 50 ml portion of saturated sodium chloride solution and then dried over anhydrous sodium sulfate, filtered and distilled on a Microvigreux column yielding the following fractions:

Provenance & Evidence