Trifluoroacetic acid → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Participants

Reaction Steps

Trifluoroacetic acid, 80.0 mL, was stirred and cooled in an ice-water bath, and 25.0 grams (0.079 mole) of 1,1-dimethylethyl N-(2,4,6-trimethylphenylsulfonyloxy)carbamate was added portionwise. Upon completion of the addition, the reaction mixture was stirred for 90 minutes, then poured into ice-water The resultant solid was collected by filtration and dissolved in diethyl ether. The solution was dried with magnesium sulfate and filtered. The solid product was precipitated from the filtrate by the addition of petroleum ether. The solid was collected by filtration, yielding 14.4 grams of 1-aminooxysulfonyl-2,4,6-trimethylbenzene. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence