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Synthesis of alkylindans

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Summary

  1. 1.

    Reaction between indan and olefins, namely propene and 1-butene, in presence of anhydrous aluminum chloride proceeds with formation of high yields of the corresponding monoand di-alkylmdans substituted in the aromatic nucleus. Under the same conditions isopropylindan and propene give triisopropylindan.

  2. 2.

    Reaction between indan and 2-methyl-2-butene under the same conditions proceeds with much greater difficulty. The yield of the alkylindan is much lower. Higher alkylation products are not formed. Reaction between these hydrocarbons in presence of BF3.H3PO4 as catalyst proceeds analogously.

  3. 3.

    Isopropyl-, diisopropyl-, triisopropyl, sec-butyl-, di-sec-butyl-, and amyl-indans, each having their substituents in the aromatic nucleus, were prepared. With the exception of isopropylindan, all these hydrocarbons were prepared for the first time.

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Literature cited

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Topchiev, A.V., Pokrovskaya, E.S. & Stepantseva, T.G. Synthesis of alkylindans. Russ Chem Bull 8, 1887–1893 (1959). https://doi.org/10.1007/BF00914762

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Keywords

  • Aluminum
  • Chloride
  • Indan
  • Hydrocarbon
  • Propene