Phenolates

They may be formed by reaction of phenols with strong base.

The phenoxide anion (aka phenolate) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines.

[3] Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see Thermodynamic versus kinetic reaction control).

Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control.

[4] Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide:[5] Salicylic acid is produced in the Kolbe–Schmitt reaction between carbon dioxide and sodium phenolate.