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 Benz[a]anthracene: Reduction of Quinones with Hydriodic acid
  • Benz[a]anthracene: Reduction of Quinones with Hydriodic acid
  • Benz[a]anthracene (CAS no ), which is also known as 1,2-benzanthracene, could be produced through the following synthetic routes.

    Caution! has been identified as a carcinogen; OSHA has issued emergency standards on its use. All procedures involving benzene should be carried out in a well-ventilated hood, and glove protection is required. Benz[a]anthracene is also a known carcinogen.

    A 500-mL, one-necked, round-bottomed flask is equipped with a magnetic stirring bar and an efficient condenser, and charged with 10.3 g (0.04 mol) of benz[a]anthracene-7,12-dione, 5 g (0.16 mol) of red phosphorus, and 100 mL of glacial acetic acid. The stirred suspension is heated to reflux, and 60 mL of 56% hydriodic acid (ca. 0.44 mol) is introduced through the condenser. The suspension is heated at reflux for 24 hr. The hot reaction mixture is poured into 500 mL of distilled water containing 30 g of sodium bisulfite. The suspension is stirred for 16 hr and filtered. The dry filter cake is transferred to a beaker and treated with sufficient hot dichloromethane (120 mL) to dissolve all of the benz[a]anthracene, and the mixture is filtered once again to remove the residual phosphorus. The volume of the filtrate is reduced to 40 mL. The solution is adsorbed on basic alumina, activity I. A 2-cm × 40-cm chromatography column is slurry-packed with ca. 10 g of basic alumina and the benz[a]anthracene adsorbed on alumina is added to the top of the column. Elution with 5% benzene in hexane (occasional rinsing of the column tip with benzene to remove crystallized product may be necessary) and evaporation of the solvent in a rotary evaporator affords 7.7–7.9 g (84–87%) of pure, white benz[a]anthracene, mp 159.5–160°C.


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