Methane → 2-(Sulfamoyloxy)benzoic acid

Participants

Reaction Steps

To a suspension of 2-[[(phenylmethyl)aminosulfonyl]oxy]benzoic acid (phenylmethyl)ester sodium salt (35.3 g, 0.076 mole) in methanol (500 ml) was added 6.2 ml of concentrated hydrochloric acid and 2 g of 5% palladium on carbon catalyst wetted with methanol (50 ml). The mixture was hydrogenated for 4 hr and filtered. The filtrate was concentrated to an oil and resuspended in THF. The solids were removed by filtration and the filtrate concentrated. The residue was triturated with 1,1,1-trichloroethane, giving 8.82 g of light purple solid. The solid was dissolved in THF, treated with activated charcoal, filtered, and concentrated again. The residue was recrystallized from 1,1,1-trichloroethane to give 6.5 g of white solid, mp 139°-140° C.

Provenance & Evidence