Acetic Acid → 2-Fluoro-5-methyl-4-nitrophenol

Participants

Reaction Steps

A solution of 26.6 grams (0.21 mole) of the fluorophenol in 63 ml. of acetic acid and 8.5 ml. of sulfuric acid was stirred at 8°-12° C. While the mixtute was cooled and stirred, a solution of 15 grams of sodium nitrite in 42 ml. of water was added dropwise over a period of about 1 hour. Stirring was continued for an additional 30 minutes. The mixture then was poured into a large volume of ice water. The resulting crude product was collected by filtration, thoroughly washed with water, and air dried while on the filter. The resulting crude nitroso compound then was added in portions to a stirred solution of 20 ml. of 70 percent nitric acid and 60 ml. of water maintained at 40°-50° C. Heating and stirring were continued until the evolution of brown fumes became negligible. The mixture then was poured into ice water, and the crude product was collected. The crude product then was recrystallized from ethanol-water to obtain a first and a second crop. A total of 25.4 grams (70 percent) of 2-fluoro-4-nitro-5-methylphenol was obtained, m.p. 110°-111.5° C.

Provenance & Evidence