Chlorosulfonic acid → Methyl [4-(chlorosulfonyl)-3,5-dimethylphenoxy]acetate

Participants

Reaction Conditions

Reaction Steps

Methyl (3,5-dimethylphenoxy)acetate (19.4 g, 0.10 mol) was added dropwise over ca. 30 min to rapidly stirred chlorosulfonic acid (58 g, 0.50 mol)that was cooled in a −20° C. bath. After an additional 20 min, the mixture was allowed to slowly warm to room temperature. After 2 hr, the mixture was poured slowly into 400 mL of ice/water. This suspension was extracted with 400 mL of dichloromethane, and the organic layer was washed with water and concentrated. The residue was purified by flash silica gel chromatography (hexanes→dichloromethane) to yield 7.6 g (27%) of the title compound.

Provenance & Evidence