What is the mechanism of the above reaction? I have thought of one possibility:
Would this work? How exactly is the chlorine installed on the alkyl chain?
$\begingroup$
$\endgroup$
1
asked Oct 18, 2015 at 12:55
-
$\begingroup$ The actual mechanism turns out to be in different order when you use ZnCl2 instead of AlCl3. It is probably the same case here. See: en.wikipedia.org/wiki/Blanc_chloromethylation $\endgroup$– wuschiCommented Oct 18, 2015 at 13:40
Add a comment
|
1 Answer
$\begingroup$
$\endgroup$
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.
