Water → 5-Chloro-2-hydroxy-3-nitrobenzoic acid

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Reaction Steps

The following procedure demonstrates the preparation of compound 1 with X=5−Cl, with comparable procedures being useful for obtaining related compounds having different X. A solution suspension of 10 g of 5-chlorosalicylic acid in 50 ml glacial acetic acid was cooled in an ice bath until the solvent began to freeze. The bath was exchanged to a room temperature water bath and 4.47 g of 90% fuming nitric acid (1:1 equivalent) in 3 ml glacial acetic acid was added dropwise. After addition was complete, the mixture was stirred for 150 minutes at room temperature (R. T.) in the water bath. It was then poured into 120 ml of ice. and water and stirred in an ice bath for 30 minutes. The precipitated solid was collected by filtration and air-dried overnight.

Provenance & Evidence