Sulfamic Acid → 2-(4-Iodophenyl)propanoic acid

Participants

Reaction Steps

To a solution of 34 g of 2-(4-iodophenyl)propionaldehyde in 100 ml of ethylene chloride was added a solution of 16.5 g of sulfamic acid in 85 ml of water. To the mixture was added dropwise with stirring a solution of 15.2 g of sodium chlorite in 22 ml of water, while maintaining the temperature at 10° to 15° C. After stirring for 10 minutes, about 15 g of sodium hydrogensulfite was added in small portions to the mixture. The organic layer was separated, washed with water, and mixed with 150 ml of 1 N sodium hydroxide solution. The aqueous layer was separated and adjusted to pH 3.0 with 6 N hydrochloric acid to precipitate white crystals. The crystals were collected by filtration, washed with water, and dried to obtain 34 g (94% yield) of 2-(4-iodophenyl)propionic acid.

Provenance & Evidence