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 Synthesis of 9-Nitroanthracene
  • Synthesis of 9-Nitroanthracene
  • 9-Nitro (CAS NO.: ), which is also known as Anthracene, 9-nitro-, could be produced through the following synthetic routes.

    Synthesis of 9-Nitroanthracene

    Twenty grams (0.112 mole) of finely powdered anthracene is suspended in 80 ml. of glacial acetic acid in a 500-ml. three-necked round-bottomed flask fitted with a 150-ml. dropping funnel, a thermometer, and an efficient motor-driven stirrer. The flask is immersed in a water bath at 20–25°, and 8 ml. (0.126 mole) of concentrated nitric acid (70% by weight, sp. gr. 1.42), essentially free of oxides of nitrogen, is added slowly from the dropping funnel with vigorous stirring. The rate of addition is controlled so that the reaction temperature does not exceed 30°. About 15–20 minutes is required for this step.

    After all the nitric acid has been added, the mixture is stirred until a clear solution is obtained (about 30 minutes), and stirring is then continued for an additional 30 minutes. The solution is filtered to remove any anthracene, and a mixture of 50 ml. (0.60 mole) of concentrated hydrochloric acid (37% by weight, sp. gr. 1.19) and 50 ml. of glacial acetic acid is added slowly to the filtrate with vigorous stirring. The pale-yellow precipitate of 9-nitro-10-chloro-9,10-dihydroanthracene which forms is separated by suction filtration on a sintered-glass funnel and is washed with two 25-ml. portions of glacial acetic acid and then with water until the washings are neutral. The product is removed from the funnel and triturated thoroughly with 60 ml. of warm (60–70°) 10% sodium hydroxide solution. The crude orange nitroanthracene is separated from the warm slurry by suction filtration and is treated with four 40-ml. portions of 10% sodium hydroxide solution. The product is finally washed thoroughly with warm water until the washings are neutral to litmus. This treatment requires about 1.5–2 l. of water. The crude 9-nitroanthracene is air-dried and recrystallized from glacial acetic acid. The yield of bright orange-yellow needles is 15–17 g. (60–68%), m.p. 145–146°.


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