11
$\begingroup$

Overall reaction

What is the mechanism of the above reaction? I have thought of one possibility:

proposed mechanism

Would this work? How exactly is the chlorine installed on the alkyl chain?

$\endgroup$
11
$\begingroup$

This reaction is chloromethylation, similar to Blanc chloromethylation, but using $\ce{AlCl3}$ as co-catalyst instead of $\ce{ZnCl2}$. These are reactions belonging to a group related to Friedel-Crafts reactions, but characterized by usage of protonation instead of coordination with molecular Lewis acids

Mechanism of your reaction (not accounting for influence of co-catalyst) can be written as:

 (source)

$\ce{AlCl3}$ coordinates to $\ce{HCl}$ creating adduct ($\ce{HAlCl4}$) which is much stronger acid.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.