View source for Sodium phenoxide

{{Chembox
| ImageFile = Fenolan sodu.svg
| ImageSize = 75px
| ImageAlt = 
| IUPACName = 
| OtherNames = Sodium phenolate
|Section1={{Chembox Identifiers
| CASNo = 139-02-6
|  PubChem = 4445035
|  ChemSpiderID = 8420
|  SMILES = c1ccc(cc1)[O-].[Na+]
|  InChI = 1/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1
|  InChIKey = NESLWCLHZZISNB-REWHXWOFAP
|  StdInChI = 1S/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1

|  StdInChIKey = NESLWCLHZZISNB-UHFFFAOYSA-M }}
|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>5</sub>NaO
| MolarMass = 116.09 g/mol
| Appearance = White solid
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards = Harmful, Corrosive
| FlashPt = Nonflammable
| AutoignitionPt = Nonflammable }}
}}

'''Sodium phenoxide''' ('''sodium phenolate''') is an [[organic compound]] with the formula NaOC<sub>6</sub>H<sub>5</sub>.  It is a white crystalline solid. Its anion, phenoxide, also known as phenolate, is the [[conjugate base]] of [[phenol]].  It is used as a precursor to many other organic compounds, such as aryl [[ether]]s.

==Synthesis and structure==
Most commonly, solutions of sodium phenoxide are produced by treating phenol with sodium hydroxide.<ref name=Speed>{{cite journal|authors=C. S. Marvel, A. L. Tanenbaum|title=γ-Phenoxypropyl Bromide|journal=Org. Synth.|year=1929|volume= 9|pages=72|doi=10.15227/orgsyn.009.0072}}</ref>  Anhydrous derivatives can be prepared by combining phenol and sodium:
:Na +  HOC<sub>6</sub>H<sub>5</sub>   →   NaOC<sub>6</sub>H<sub>5</sub>  +  1/2 H<sub>2</sub>

Like other sodium [[alkoxide]]s, crystalline sodium phenolate adopts a complex structure involving multiple Na-O bonds.  Solvent-free material is polymeric, each Na center being bound to three oxygen ligands as well as the [[phenyl ring]].  Adducts of sodium phenoxide are molecular, such as the [[cubane-type cluster]] [NaOPh]<sub>4</sub>([[HMPA]])<sub>4</sub>.<ref>Michael Kunert, Eckhard Dinjus, Maria Nauck, Joachim Sieler "Structure and Reactivity of Sodium Phenoxide - Following the Course of the Kolbe-Schmitt Reaction" Chemische Berichte 1997 Volume 130, Issue 10, pages 1461–1465. {{DOI|10.1002/cber.19971301017}}</ref>

Sodium phenoxide can be produced by the "alkaline fusion" of [[benzenesulfonic acid]], whereby the sulfonate groups are displaced by hydroxide:
:C<sub>6</sub>H<sub>5</sub>SO<sub>3</sub>Na  + 2 NaOH  →  C<sub>6</sub>H<sub>5</sub>ONa  +  Na<sub>2</sub>SO<sub>3</sub>
This route once was the principal industrial route to phenol.

[[File:Sodium-phenoxide-Na-coordination-3D-balls.png|200px|right|thumb|Subunit of the struture of solvent-free sodium phenoxide, illustrating the binding of phenoxide to sodium through both the arene and the oxygen.]]

==Reactions==
Sodium phenoxide is a moderately strong base.  Acidification gives phenol:<ref>{{March6th}}</ref>
:PhOH  &#x21CC;  PhO<sup>−</sup>  +  H<sup>+</sup>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(K = 10<sup>−10</sup>)

Alkylation affords phenyl ethers:<ref name=Speed/>
:NaOC<sub>6</sub>H<sub>5</sub>  +  RBr →   ROC<sub>6</sub>H<sub>5</sub>  +  NaBr
The conversion is an extension of the [[Williamson ether synthesis]].  With acylating agents, one obtains esters:
:NaOC<sub>6</sub>H<sub>5</sub>  +  RC(O)Cl →   RCO<sub>2</sub>C<sub>6</sub>H<sub>5</sub>  +  NaCl

Sodium phenoxide is susceptible to certain types of [[electrophilic aromatic substitution]]s. For example, it reacts with carbon dioxide to form 2-hydroxybenzoate, the conjugate base of [[salicylic acid]].  In general however, electrophiles irreversibly attack the oxygen center in phenoxide.
[[image:Kolbe-Schmitt.png|500px|center|The [[Kolbe–Schmitt reaction]].]]

==References==
<references />

==External links==
{{commons category inline}}

[[Category:Phenols]]
[[Category:Organic sodium salts]]