[mizna.z]

To make 2,4,6-trimethylbenzyl chloride, I have to use 1,3,5-trimethylbenzene and react it with formaldehyde and HCl.
Ive gotten started but now im stuck.

So the H-Cl protonates the formaldehyde making that carbon delta positive. this carbon can now be attacked by one of the carbons of the 1,3,5-trimethylbenzene at any of the available spots. creating an OH where the Cl needs to be. How do i get rid of the OH now in order for the Cl to attack?

I was thinking of protonating the OH with another molecule of HCl and then allowing an SN2 reaction to take place so the Cl can attack and replace the OH.

But i have a feeling that I've done something wrong?

[jpg28]

I'm fine with the first part of your proposed mechanism (the protonation of the aldehyde); however, I don't think that a (any) carbon atom on your 1,3,5-trimethylbenzene will be able to attack your carbonyl carbon even if it is partially (delta) positive. None of your carbons (in 1,3,5-trimethylbenzene or sometimes referred to as mesitylene) are nucleophilic...

[Fleaker]

Make sure you're very careful when you're using CHO with HCl--chloromethyl ethers are potent carcinogens.