Tuesday, June 25, 2019

organic chemistry - Mechanism for chloromethylation of benzene with formaldehyde and HCl


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?



Answer



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.


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