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Intramolecular Friedel–Crafts cyclization

6 real reactions from the literature, on alkylbenzenes, benzylic alcohols, trisubstituted alkenes and anisoles. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Friedel–Crafts cyclization: 1-methoxy-2-(3-methylbut-2-en-1-yl)benzene (a trisubstituted alkene) with AlCl3; HCl gives 7-methoxy-3,3-dimethyl-1,2-dihydroindene (the fused ring). 60% yield.
    Friedel–Crafts cyclizationBull. Soc. Chim. Belg. 1981, 90, 847

  2. Friedel–Crafts cyclization: 4-phenylbutanoyl chloride (an alkylbenzene) with AlCl3; CS2, Δ gives 1-tetralone (the fused ring).
    Friedel–Crafts cyclizationOrg. Synth. Coll. Vol. 2, p. 569

  3. Friedel–Crafts cyclization: an anisole with 1); SOCl2; 2); AlCl3 gives 6-hexoxy-1-benzothiophen-3-one (the fused ring). 62% yield.
    Friedel–Crafts cyclizationTetrahedron Lett. 1994, 35, 7549

  4. Friedel–Crafts cyclization: a benzylic alcohol with H2SO4 gives the fused ring. 85% yield.
    Friedel–Crafts cyclizationJ. Org. Chem. 1973, 38, 1909

  5. Friedel–Crafts cyclization: a benzylic alcohol with H2SO4 gives the fused ring. 70% yield.
    Friedel–Crafts cyclizationJ. Org. Chem. 1973, 38, 1909

  6. Friedel–Crafts cyclization: 4-phenylbutyric acid (an alkylbenzene) with polyphosphoric acid; Δ gives 1-tetralone (the fused ring).
    Friedel–Crafts cyclizationOrg. Synth. Coll. Vol. 3, p. 798