Phenolates
Phenolates (also called phenoxides) are anions, salts, and esters of phenols. They may be formed by reaction of phenols with strong base.[1]
Properties
Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions.[2] At pH = 10, phenol and phenolate are in approximately 1:1 proportions.
Phenolate anions are enolates. As such, they react as nucleophiles at both oxygen and carbon positions.[3] In general, reaction at oxygen occurs under kinetic control, whereas reaction at carbon occurs under thermodynamic control.
Uses
Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide:[4]
- 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
- ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 506, ISBN 978-0-471-72091-1
- ^ Jakubke, Hans-Dieter; Karcher, Ruth (1999). Lexikon der Chemie in drei Bänden, Band 3. Heidelberg: Spektrum Verlag. p. 14. ISBN 3-8274-0381-2.
- ^ Mayer, Robert J.; Breugst, Martin; Hampel, Nathalie; Ofial, Armin R.; Mayr, Herbert (2019-07-19). "Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities". The Journal of Organic Chemistry. 84 (14): 8837–8858. doi:10.1021/acs.joc.9b01485. ISSN 0022-3263.
- ^ Beyer, Hans; Walter, Wolfgang (1984). Organische Chemie. Stuttgart: S. Hirzel Verlag. pp. 463–464. ISBN 3-7776-0406-2.
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