In the Reimer-Tiemann reaction (phenol, CHCl3, aqueous NaOH, then acid), the electrophile that attacks the phenoxide ring is

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In the Reimer-Tiemann reaction (phenol, $CHCl X_{3}$ , aqueous $NaOH$ , then acid), the electrophile that attacks the phenoxide ring is

Hydroxide deprotonates

CHCl X_{3}

to give

CCl X_{3} X^{-}

, which loses chloride to form

: CCl X_{2}

. The electron-rich phenoxide ring attacks this electrophilic carbene, mainly at the ortho position. Hydrolysis of the

- CHCl X_{2}

group then gives the aldehyde, salicylaldehyde.