Isopropanol → 5-Amino-2-chlorophenol

Participants

Reaction Steps

A suspension (about 600 ml) containing 100 g of reduced iron, 5 g of ammonium chloride, 500 ml of isopropyl alcohol, and 100 ml of water was refluxed with vigorous stirring. To this suspension was added 100 g of 2-chloro-5-nitrophenol in portions. After completion of the addition, the mixture was heated for an additional 1 hour. This suspension was filtered when hot with the aid of Celite and the filtrate was washed with about 500 ml of hot isopropyl alcohol and then concentrated to about one-fifth its original volume under reduced pressure. To the concentrate was added 1 l of ice water and the resulting crystalline precipitate was collected by filtration and washed with water.

Provenance & Evidence