2-Methylbenzenesulfonic acid → 2-Chloromethyl-4,4,6,6-tetramethyl-1,3-dithiane

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Reaction Steps

2-Chloro-1,1-dimethoxyethane (0.1 mole) and 2,4-dimethyl-2,4-pentanedithiol (0.1 mole) are charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer, Dean Stark trap and reflux condenser. Toluene sulfonic acid (0.1 grams) is added and the reaction mixture is heated and thiol removed. When the thiol evolution ceases, the reaction mixture is then cooled to room temperature, treated with sodium carbonate (5 grams) and filtered. Volatiles are stripped from the filtrate using a rotary evaporator to yield the desired product 2-chloromethyl-4,4,6,6-tetramethyl-1,3-dithiane as the residue.

Provenance & Evidence