Acetic Acid → Styrenesulfonic acid

Participants

Reaction Steps

13.0 g of aniline-2-sulphonic acid were suspended in 200 ml of methanol and treated with 20 g of glacial acetic acid. Under a nitrogen atmosphere, 9.5 g of amyl nitrite were added dropwise at a temperature of 0° to 5° C. and the suspension was stirred for 1 hour. A solution of 15 g of NaOH in 100 ml of methanol was then added dropwise at such a rate that the temperature of the mixture did not exceed 20° C. After addition of 0.5 g of bis(dibenzylideneacetone)palladium(0), the mixture was stirred at 20° C. for 3 hours under an ethylene pressure of 20 bar, the solid was then filtered off with suction and the filtrate was evaporated to dryness. 12.1 g (78%) of styrene-2-sulphonic acid, Na salt, were obtained.

Provenance & Evidence