7
$\begingroup$

When discussing the Gattermann–Koch reaction on phenol substrates, it has been said that O-acylation is a problematic competing reaction as

in a phenol, there's high electron density on the O atom [...]

However, there are also numerous other reactions where phenol reacts with electrophiles on the benzene ring. Some examples are:

Why is the Gatterman–Koch reaction an exception?

Improve this question
$\endgroup$
3
  • $\begingroup$ Can anyone please explain what's wrong with my question? $\endgroup$
    – jyoti proy
    Sep 13, 2017 at 21:13
  • $\begingroup$ There isn't really any literature evidence to support the fact that it does react @ oxygen (though it is quite probable). In the Gattermann-Koch mechanism, the intermediate is highly reactive, the Gattermann modification avoids this, making it amenable to synthesis (Gattermann conditions + phenol are fine and have been used in many syntheses). The original Gatterman report of phenols not being amenable to G-K conditions is @ DOI: 10.1002/jlac.19073570209 (German language, very hard to decipher), DOI:10.1002/0471264180.or009.02 also has an overview (English language). $\endgroup$
    – NotEvans.
    Sep 15, 2017 at 19:47
  • $\begingroup$ @NotEvans. I've read the abstract of the English version which says that the Gattermann reaction with $\ce{CN}$ as a reagent reacts on benzene, but I am confused about the Gattermann koch version. $\endgroup$
    – jyoti proy
    Sep 15, 2017 at 20:21

0

Reset to default

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge that you have read and understand our privacy policy and code of conduct.