Chlorosulfonic acid → HCID 13646248, compound

Participants

Reaction Steps

A mixture of 15.8 g (0.086 mol) of methyl 4-chloro-2-methylbenzoate (2) and 25.8 ml (45.2 g, 0.39 mol) of chlorosulfonic acid was heated to a gentle reflux under nitrogen. After 3 hrs., the mixture was cooled and poured slowly into an ice-water mixture. After stirring for 1 hr., the mixture was filtered and rinsed well with ice cold water. Drying in a vacuum oven (60° C.) gave 17.4 g (0.065 mol, 75% yield) of the sulfonylated acid (off-white crystals). A mixture of 14.5 g of the acid and 2 drops of dimethylformamide in 50 ml of thionyl chloride was heated to reflux under nitrogen. After 11/2 hrs., the solvent was removed under reduced pressure. Methanol (125 ml) was added to residue material and the solution was cooled to 10° C. After 5 hrs., the solid was filtered and airdried, giving 12.8 g of off-white crystals (3); m.p. 94.5° -96° C.

Provenance & Evidence