Gatterman – Koch reaction. The aim of the reaction is to attach a carbonil group on an aromatic system. Here is the overall reaction: Reazione di gattermann koch . PDF | Descriptive data on Gatterman-koch reactions. Title, The Gattermann-Koch Reaction. Author(s), Crounse, Nathan N. Volume, 5. Year of Publication, DOI, /or
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What I don’t understand about this reaction is that according to Wikipedia along with other online texts I’ve used, the Gattermann-Koch reaction is inapplicable to gattermaann substrates. The drawback has been left unexplained by all my resources online and textbooks and even my professor was oblivious to it.
I am unable to understand why the reaction doesn’t apply to phenol and what exact side reactions might occur.
The Gattermann-Koch Reaction is not applicable to phenol and phenol ethers because they “could not be successfully formylated at atmospheric pressure in benzene as a solvent.
You have outlined that the formyl chloride is generated as the reactive, electrophilic intermediate under these conditions. Phenol can act as Lewis base and form adduct with AlCl3, using a lone pair on the O atom, hence deactivating the ring for further reaction.
I suspect that, in the presence of the Lewis Acid catalyst, even if a formyl ester is formed, it will rearrange the the acylbenzene, which is irreversible. This may have consequences for the o,p-product ratio, And as far as the cuprous chloride, use aluminum trichloride. And you could make the Scylla bromide first, with Formica acid an bromine.
Much more reactive will likely form the sculpture ester first, in catalyze. Then catalyst to rearrange it.
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organic chemistry – Gattermann-Koch Reaction with Phenol Substrates – Chemistry Stack Exchange
I didn’t consider that, but then why would that only apply for phenol substrates? Wouldn’t amines and ethers also be reactive gatfermann the same manner?
In the case of phenols, we’d use the Reimer-Tiemann or the Duff reaction instead. How sure can we be that we actually have formyl chloride as a reactive intermediate? Also cuprous chloride seems to play an important role in the mechanism.
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Terry Lee Davis 1. Are you simply trying to put obscure words in last sentences? I know what Scylla is and it’s not some wacky mythology chemistry here I have to agree, this looks like an autocorrect nightmare.
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Gattermann-Koch Reaction – Organic Reactions Wiki