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 Synthesis of o-Nitroacetophenone
  • Synthesis of o-Nitroacetophenone
  • o-Nitro (CAS NO.: ), which is also known as Acetophenone, 2'-nitro-, could be produced through the following synthetic routes.

    Synthesis of o-Nitroacetophenone

    In a 500-ml. three-necked round-bottomed flask equipped with a mercury-sealed stirrer, a dropping funnel, and a reflux condenser (protected by a drying tube) is placed 5.4 g. (0.22 g. atom) of magnesium turnings. Five milliliters (0.085 mole) of absolute ethanol and 0.5 ml. of carbon tetrachloride are added. If the reaction does not start immediately, the flask is ed for a short time on a steam bath. After the reaction has proceeded for several minutes, 150 ml. of absolute ether is added cautiously with stirring. A solution of 35.2 g. (0.22 mole) of diethyl malonate, 20 ml. (0.34 mole) of absolute ethanol, and 25 ml. of absolute ether is added with stirring at such a rate that rapid boiling is maintained; heat is supplied when necessary. The mixture is heated under reflux on a steam bath for 3 hours, at which time most of the magnesium has dissolved. To the gray solution is added 37 g. (0.2 mole) of o-nitrobenzoyl chloride, dissolved in 50 ml. of ether, in a period of 15 minutes. Heating under reflux on the steam bath is continued throughout the addition of the o-nitrobenzoyl chloride and until the green solution becomes too viscous to stir. The reaction mixture is cooled and shaken with dilute sulfuric acid (25 g. of concentrated sulfuric acid in 200 ml. of water) until all the solid has dissolved.

    The ether phase is separated and the aqueous layer extracted with 75 ml. of ether. The ether extracts are combined and washed with water, and the solvent is removed by distillation.

    To the crude diethyl o-nitrobenzoylmalonate is added a solution of 60 ml. of glacial acetic acid, 7.6 ml. of concentrated sulfuric acid, and 40 ml. of water, and the mixture is heated under reflux for 4 hours or until no more carbon dioxide is evolved. The reaction mixture is chilled in an ice bath, made alkaline with 20% sodium hydroxide solution, and extracted with several portions of ether. The combined ethereal extracts are washed with water and dried with anhydrous sodium sulfate followed by Drierite, and the solvent is removed by distillation. On fractional distillation of the residue, 27.0–27.4 g. (82–83%) of light-yellow o-nitroacetophenone boiling at 158–159° /16 mm. is obtained (n25D 1.548, n20D 1.551, d254 1.236).


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