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

Participants

Reaction Steps

In 100 ml of ethylene chloride was dissolved 34 g of 2-(4-iodophenyl)propionaldehyde, and a solution of 16.5 g of sulfamic acid in 85 ml of water was added to the solution. A solution of 15.2 g of sodium chlorite in 22 ml of water was then dropped thereinto while keeping the solution at 10° to 15° C. The solution was stirred for 10 min, and 15 g of sodium hydrogen sulfite was added portionwise thereto. The organic layer was separated and then washed with water. To the organic layer was added 150 ml of 1 N aqueous sodium hydroxide solution, and the aqueous layer was then separated, after which the pH of the aqueous layer was adjusted to 3.0 with 6 N hydrochloric acid, upon which white crystals were precipitated. The crystals were collected by filtration, washed with water and then dried to obtain 34 g (yield 94%) of 2-(4-iodophenyl)propionic acid.

Provenance & Evidence