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Friedel–Crafts alkylation

6 real reactions from the literature, on carbazoles, six-membered cycloalkenes, benzylic alkyl chlorides and benzene. 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 alkylation: carbazole with (excess); AlCl3 gives 3,6-di-tert-butylcarbazole (the alkylated arene). 72% yield.
    Friedel–Crafts alkylationJ. Phys. Chem. C 2017, 121, 23618

  2. Friedel–Crafts alkylation: cyclohexene (a six-membered cycloalkene) with H2SO4 gives cyclohexylbenzene (the alkylated arene).
    Friedel–Crafts alkylationOrg. Synth. Coll. Vol. 2, p. 151

  3. Friedel–Crafts alkylation: benzyl chloride (a benzylic alkyl chloride) with Al(Hg), Δ gives diphenylmethane (the alkylated arene).
    Friedel–Crafts alkylationOrg. Synth. Coll. Vol. 2, p. 232

  4. Friedel–Crafts alkylation: benzene with BF3 gives tert-amylbenzene (the alkylated arene). 96% yield.
    Friedel–Crafts alkylationJ. Am. Chem. Soc. 1959, 81, 1110

  5. Friedel–Crafts alkylation: phenyl(2-thienyl)methanol (a thiophene) with H2SO4 gives 4-[phenyl(thiophen-2-yl)methyl]phenol (the alkylated arene).
    Friedel–Crafts alkylationRealOChem worksheet

  6. Friedel–Crafts alkylation: p-cresol (a phenol) with butylated hydroxytoluene gives 2,6-di-tert-butyl-4-methylphenol (the alkylated arene).
    Friedel–Crafts alkylationRealOChem worksheet