Water → 3-Fluoro-4-nitrobenzoic acid

Participants

Reaction Steps

A solution of 3-fluoro-4-nitrotoluene (2 g, 12.82 mmole) in 13 mL water, containing 5.72 g of Na2Cr2O7, was treated dropwise with 14.2 mL of concentrated sulfuric acid, stirred at room temperature for one hour and then diluted with 20 mL of water. The mixture was filtered and the recovered solid was gently heated in 50 mL 2% sodium hydroxide solution. The resulting solution was cooled and filtered and the filtrate was acidified with concentrated HCl. The aqueous phase was extracted with two 100 mL portions of ethyl acetate, the combined extracts were washed with 100 mL of aqueous saturated sodium chloride solution, dried over MgSO4, filtered and concentrated in vacuo to give 1.6 g (68%) of 3-fluoro-4-nitrobenzoic acid as a yellow solid.

Provenance & Evidence