Sodium Hydroxide → 2-Fluoro-4-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A 3L 3-necked flask equipped with a magnetic stirrer was charged with 25.00 g of 2-fluoro-4-nitrotoluene (Aldrich Chemical Co., Milwaukee, Wis., 53233), 1.65 L of 1 N NaOH, and 25.00 g of KMnO4. The resulting mixture was heated to 95° C. with stirring. Additional 25.00 g portions of KMnO4 were added after 1 h and 2 h. After stirring at 95° C. for an additional hour the reaction mixture was cooled to RT and filtered through celite to remove MnO2. The filtrate was concentrated in vacuo to 500 mL and acidified to pH 2 by addition of concentrated H2SO4. A yellow-orange precipitate formed which was collected by vacuum filtration. The crude solid was dissolved in 300 mL of 1 N aqueous NaOH, acidified to pH 2 and the mixture extracted with CH2Cl2 (4×150 mL). The combined CH2Cl2 extracts were washed with 0.1 N aqueous HCl (2×100 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to afford 12.44 g (42%) of 2-fluoro-4-nitrobenzoic acid as a yellow crystalline solid, m.p. 165-167° C.

Provenance & Evidence