Perchloric Acid → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Participants

Reaction Conditions

Reaction Steps

Under argon atmosphere, (Z)-ethyl N-mesitylsulfonyloxyacetimidate (15 g, 52.6 mmol) was dissolved in THF (13 mL) at 0° C. Perchloric acid (70% aqueous solution, 22.6 g, 13.6 mL, 158 mmol) was then added dropwise at 0-5° C. over a period of 50 min. After 10 min, precipitation started and THF (3 mL) was added. After stirring at 0° C. for 30 min, the mixture was poured into ice water (200 mL) under vigorous stirring giving a white suspension. After additional stirring for 15 min, the suspension was filtered and the precipitate was washed with ice water. The white solid was dissolved in diethyl ether (150 mL), dried over MgSO4 and evaporated at RT without heating while the flask was cooled (very important, because the compound can decompose at 25° C.!) to give O-(mesitylsulfonyl)hydroxylamine as white solid (9.2 g, 42.7 mmol, 81.3%). The crude product was used further without purification since O-(mesitylsulfonyl)hydroxylamine is unstable at 25° C.!

Provenance & Evidence