Formation of Ethers from Phenol -- Williamson Synthesis

An alkaline solution of phenol (i.e. the phenoxide ion) undergoes nucleophilic substitution on an alkyl halide to form a phenyl ether -- this is the Williamson ether synthesis applied to phenol. Phenol + NaOH gives sodium phenoxide (losing H2O); sodium phenoxide + CH3-I gives anisole (methoxybenzene) + NaI. Because the electrophile here is always an ALKYL halide (never an aryl halide, which is far too unreactive toward SN2), this route can only build the alkyl-oxygen bond of a …