A Novel Synthesis of 4-Methyl-1 : 2-Benzanthracene


OF the various alkylbenzanthracenes, 4-methyl-1 : 2-benzanthracene aroused considerable interest through its pronounced carcinogenic activity1. The literature includes a few syntheses of this hydrocarbon2, but these methods are laborious since they involve numerous steps. We have now worked out a new route to this hydrocarbon in four steps starting from 2-allylcyclohexanone and tetralin, based on the method developed by Mukherji and co-workers3 for the synthesis of polycyclic aromatic hydrocarbons.

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  1. 1

    Shear and Leiter, J. Nat. Cancer Inst., 2, 214 (1941); Chem. Abst., 1666 (1942).

  2. 2

    (a) Fieser and Jones, J. Amer. Chem. Soc., 60, 1940 (1938). (b) Cook, J. Chem. Soc., 1592 (1933). (c) Fieser and Peters, J. Amer. Chem. Soc., 54, 3742 (1932).

  3. 3

    Mukherji et al., J. Org. Chem., 17, 1202 (1952); 18, 1499 (1953); 19, 328 (1954). Curr. Sci., 23, 158 (1954).

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VIG, O., KESSAR, S. & MUKHERJI, S. A Novel Synthesis of 4-Methyl-1 : 2-Benzanthracene. Nature 174, 834 (1954). https://doi.org/10.1038/174834a0

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