# Electrophilic Substitution of Substituted Benzene

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?

• Still the same problem remains unresolved you removed O's acidic H but increased O's donating capacity. So the answer is no. Aug 19, 2021 at 19:04
• If R=CH3, anisole reacts with succinic anhydride in the presence of AlCl3 in a FC reaction. There are numerous methods for demethylating anisole and its derivatives. Aug 19, 2021 at 19:11

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-$$\ce{C^{14}}$$.
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).