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  4. Reaction of phenol with chloroform/sodium hydroxide to give o- hydroxy benzaldehyde involves the formation of

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Q. Reaction of phenol with chloroform/sodium hydroxide to give $ o- $ hydroxy benzaldehyde involves the formation of

J & K CETJ & K CET 2005Alcohols Phenols and Ethers

Solution:

Phenol reacts with chloroform and $NaOH$ to give $o-$ hydroxy benzaldehyde or salicylaldehyde. In this reaction dichlorocarbene $\left(: C C l_{2}\right)$ electrophile is generated. This reaction is called Reimer-Tiemann reaction.
$OH ^{-}+ CHCl _{3} \rightarrow HOH +\underset{\text { unstable }}{ CCl _{3}^{-}}: CCl _{3}^{-} \rightarrow Cl ^{-}+\underset{\text { dichlorocarbene }}{: CCl _{2}}$