Electrophilic Substitution of Substituted Benzene

Question

I know that phenol doesn't undergo the Friedel-Crafts Alkylation and Acylation reactions, because the reagent $\ce{AlCl3}$ forms a complex with phenol, as the oxygen atom donates it's lone pair to the Lewis acid.

Now, if I use $\ce{OR}$ group substituted instead of $\ce{OH}$, will the same comple, formation occur, or will the reaction take place?

Answer 1

Friedel-Crafts reactions of anisole is known and the relevant acylation is performed in most academic institutions during undergraduate sophomore organic chemistry laboratories. For instance, Aluminum Chloride Catalyzed Friedel-Crafts reaction of anisole with Epoxide has been published (Ref.1). The authors have performed the reaction in various solvents involving nitromethane, which is a stronger base and would have strong interaction with the Lewis acid catalysts comparable to that with the substrate:

The reaction of anisole with propylene oxide by aluminum chloride has been studied in various kinds of solvents. While the normal Friedel-Crafts reaction yielded 2-(methoxyphenyl)-1-propanols, 1,1-bis(methoxyphenyl)-propanes were also formed in this reaction; these were not obtained by the subsequent reaction of mono(methoxyphenyl) products with another anisole. The yields of 1,1-bis(methoxyphenyl)propanes increased by increasing the basicity of solvents. The mechanism of the formation of 1,1-bis(methoxyphenyl)propanes can be explained by the isomerization of epoxide to aldehyde and the subsequent condensation with anisole. Various kinds of epoxides also gave 1,1-bis(methoxyphenyl)alkanes in nitromethane.

Further, in earlier studies, the Friedel–Crafts alkylation of anisole with 2-phenylethyl chloride and 2-phenylethanol has resulted in a product, p-methoxydibenzyl. The result has showed isotope position rearrangement corresponding to an essentially 50% rearrangement of the $\ce{C^{14}}$-labeled atoms from the $\ce{C}$-1 to the $\ce{C}$-2 positions in the original chloride and alcohol when the substrates are 2-phenylethyl-1-$\ce{C^{14}}$ chloride and 2-phenylethanol-1-$\ce{C^{14}}$.

References:

1. Inoue Masashi, Sugita Toshio, and Ichikawa Katsuhiko, "Aluminum Chloride Catalyzed Friedel-Crafts Reaction of Anisole with Epoxide Accompanying Isomerization," Bulletin of the Chemical Society of Japan 1978, 51(1), 174-178 (DOI: https://doi.org/10.1246/bcsj.51.174).
2. C. C. Lee, A. G. Forman, and A. Rosenthal, "Rearrangement Studies with $\ce{C^{14}}$: III. The Friedel–Crafts alkylation of anisole with 2-phenylethyl-1-$\ce{C^{14}}$ chloride and 2-phenylethanol-1-$\ce{C^{14}}$," Canadian Journal of Chemistry 1957, 35(3), 220-225 (DOI: https://doi.org/10.1139/v57-033).