Which of the following reactions will not result in the formation of anisole?

Which of the following reactions will not result in the formation of anisole?
  1. Phenol + dimethyl sulphate in presence of a base
  2. Sodium phenoxide is treated with methyl iodide
  3. Reaction of diazomethane with phenol
  4. Reaction of methylmagnesium iodide with phenol

Solution

Phenol has active (acidic) hydrogen so it reacts with $\mathrm{CH}_{3} \mathrm{MgI}$ to give $\mathrm{CH}_{4}$, and not anisole
$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{CH}_{3} \mathrm{MgI} \longrightarrow \mathrm{CH}_{4}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OMgI}$ /

Asked in: JEE-TOPICTESTS-CHEMISTRY

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