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.{{March6th|page = 506}}
Properties
{{main|sodium phenoxide}}
Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions.{{Cite book|last1=Jakubke|first1=Hans-Dieter|title=Lexikon der Chemie in drei Bänden, Band 3|last2=Karcher|first2=Ruth|publisher=Spektrum Verlag|year=1999|isbn=3-8274-0381-2|location=Heidelberg|pages=14}} 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.[https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank2/]. 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.{{cite journal|last1=Mayer|first1=Robert J.|last2=Breugst|first2=Martin|last3=Hampel|first3=Nathalie|last4=Ofial|first4=Armin R.|last5=Mayr|first5=Herbert|date=2019-06-26|title=Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities|journal=Journal of Organic Chemistry|volume=84|issue=14|pages=8837–8858|doi=10.1021/acs.joc.9b01485|pmid=31241938|s2cid=195696760}}
Uses
Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide:{{Cite book|last1=Beyer|first1=Hans|title=Organische Chemie|last2=Walter|first2=Wolfgang|publisher=S. Hirzel Verlag|year=1984|isbn=3-7776-0406-2|location=Stuttgart|pages=463–464}}
: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.
