Phenolates

Phenolates (also called phenoxides) are , salts, and esters of phenols, containing the phenolate ion. They may be formed by reaction of phenols with strong base.

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Properties Alkali metal phenolates, such as sodium phenoxide hydrolyze in aqueous solution to form basic solutions.

(1999). 9783827403810, Spektrum Verlag. ISBN 9783827403810

At pH = 10, phenol and phenolate are in approximately 1:1 proportions.

The phenoxide anion (aka phenolate) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines.[1]. Mayr's Database of Reactivity Parameters. Retrieved July 10, 2019. 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.

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Uses Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an Haloalkane:

(1984). 9783777604060, S. Hirzel Verlag. ISBN 9783777604060

C₆H₅ONa + CH₃I → C₆H₅OCH₃ + NaI

C₆H₅ONa + (CH₃O)₂SO₂ → C₆H₅OCH₃ + (CH₃O)SO₃Na

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Production of salicylic acid Salicylic acid is produced in the Kolbe–Schmitt reaction between carbon dioxide and sodium phenolate.

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See also

• Sodium phenolate

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