I'm not convinced that aldimino/ketimino groups are ortho/para directing (or that they're compatible with FC rxn conditions in the first place!), and
your arrow-pushing diagram pulls two hydrogen atoms out of the aether, so those seem like more critical issues.
Quote: | For the amine in the friedel crafts, if you look at the more detailed post I put up this afternoon, the idea was to have the trimethylamine in ether
after the Friedel crafts cauldron. That way excess Cl2 will just pass through, but the HCl will farm an insoluble salt whose percipitate can be used
to monitor the progress of the reaction. The role of triethylamine here is more as an indicator (since PH indicators are difficult to use here because
using them in something that provides protons would generate more HCl and give false results). It's not exact, by any means, not least because some
HCl will likely pass through without forming a salt, but maybe worth a try?
| Are you aware that mixtures of ether and chlorine can explode? You can't just assume chlorine won't react
with stuff! It's very reactive!
https://drs.illinois.edu/Page/SafetyLibrary/ChemicalCompatib...
I'm not convinced that chlorine won't react with trimethylamine, either.
[Edited on 21-7-2021 by clearly_not_atara] |