Chlorosulfonic acid → 4-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

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Reaction Steps

Chlorosulfonic acid (12 ml, 184 mmol) in methylene chloride (60 ml) was slowly added dropwise to a solution, cooled to 0° C., of 3,5-dimethylanisole (5 g, 36.71 mmol) in methylene chloride (60 ml) over the course of 10 min. The reaction mixture was stirred for a further 10 min and subsequently slowly added dropwise to ice-water (300 ml) and the mixture was stirred until the ice had melted. The phases were separated and the aqueous phase was extracted with methylene chloride (50 ml). The combined organic phases were washed with saturated sodium chloride solution (50 ml), dried (Na2SO4) and concentrated in vacuo. It may be noted that the ratio of anisole/chlorosulfuric acid can be reduced to 1/2.3 without losses with respect to the yield.

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