Gattermann-Koch Reaction with Phenol Substrates The Gattermann-Koch Reaction involves the formation of an aryl aldehyde using carbon monoxide and hydrochloric acid as reactants. The reaction is catalyzed by aluminium trichloride in the presence of trace amounts of cuprous chloride.



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 phenol 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.

Additionally, why is the explanation so obscure?

[EDIT] I found the explanation. 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."
"This failure to react was attributed to the insolubility of the cuprous chloride in the reaction mixture."

Can someone please explain this in simple terms?
You have outlined that the formyl chloride is generated as the reactive, electrophilic intermediate under these conditions.

You are planning to perform an electrophilic aromatic substitution, but in a phenol, there's high electron density on the $\ce{O}$ atom. Isn't it conceivable that your main reaction product is phenylformate here, resulting from $\ce{O}$-acylation?