Phenolates
Phenolates (also called phenoxides) are anions, salts, and esters of phenols, containing the phenolate ion. They may be formed by reaction of phenols with strong base.[1]
Properties
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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]
Uses
Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide:[5]
- C6H5ONa + CH3I → C6H5OCH3 + NaI
- C6H5ONa + (CH3O)2SO2 → C6H5OCH3 + (CH3O)SO3Na
Production of salicylic acid
Salicylic acid is produced in the Kolbe–Schmitt reaction between carbon dioxide and sodium phenolate.
See also
References
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