# Mesitol

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Mesitol
> Markdown URL: https://mediated.wiki/source/Mesitol.md
> Source: https://en.wikipedia.org/wiki/Mesitol
> Source revision: 1159818647
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Chembox
<!-- Images -->
|ImageFile = Mesitol_V1.svg
|ImageSize = 150px
<!-- Names -->
|PIN = 2,4,6-Trimethylphenol
|OtherNames = Hydroxymesitylene; Mesityl alcohol
<!-- Sections -->
|Section1 = {{Chembox Identifiers
|CASNo = 527-60-6
|PubChem = 10698
|UNII = FPZ32614N6
|ChemSpiderID = 10248
|EC_number = 208-419-2
|SMILES = Cc1cc(c(c(c1)C)O)C
|StdInChI = 1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3
|StdInChIKey = BPRYUXCVCCNUFE-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
|C=9 | H=12 | O=1
|Appearance = white solid
|MeltingPtC = 70-72
|MeltingPt_ref = <ref name=SA>{{cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/w432900 | publisher = [Sigma-Aldrich](/source/Sigma-Aldrich) | title = 2,4,6-Trimethylphenol }}</ref>
|BoilingPtC = 220
|BoilingPt_ref = <ref name=SA/>
|Solubility = 1.01 g/l
}}
|Section3 = {{Chembox Hazards
|GHSPictograms = {{GHS05}}{{GHS09}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|314|411}}
|PPhrases = {{P-phrases|260|264|273|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|391|405|501}}
}}
}}

'''Mesitol''' ('''2,4,6-trimethylphenol''') is an [organic compound](/source/organic_compound) with the formula (CH<sub>3</sub>)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>OH. It is one of several isomers of [trimethylphenol](/source/trimethylphenol). The name and structure of mesitol derives from the combination of [mesitylene](/source/mesitylene) and [phenol](/source/phenol).

==Synthesis==
Mesitol is the main product from the methylation of phenol with methanol in the presence of a solid acid.<ref>{{Ullmann |doi=10.1002/14356007.a19_313|title=Phenol Derivatives|year=2000|last1=Fiege|first1=Helmut|last2=Voges|first2=Heinz-Werner|last3=Hamamoto|first3=Toshikazu|last4=Umemura|first4=Sumio|last5=Iwata|first5=Tadao|last6=Miki|first6=Hisaya|last7=Fujita|first7=Yasuhiro|last8=Buysch|first8=Hans-Josef|last9=Garbe|first9=Dorothea|last10=Paulus|first10=Wilfried|isbn=3527306730}}</ref> 

It can also be obtained by reaction of mesitylene with [peroxymonophosphoric acid](/source/peroxymonophosphoric_acid):<ref>{{Cite journal | doi = 10.1016/S0040-4020(01)92087-3| title = Aromatic hydroxylation with peroxymonophosphoric acid| journal = Tetrahedron| volume = 37| issue = 8| pages = 1485| year = 1981| last1 = Ogata| first1 = Yoshiro| last2 = Sawaki| first2 = Yasuhiko| last3 = Tomizawa| first3 = Kohtaro| last4 = Ohno| first4 = Takashi}}</ref>

:left|300px{{clear-left}}

An alternative route involves palladium-catalyzed reaction of bromomesitylene with potassium hydroxide.<ref>{{cite journal |doi=10.1021/ja0639719|title=The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans|year=2006|last1=Anderson|first1=Kevin W.|last2=Ikawa|first2=Takashi|last3=Tundel|first3=Rachel E.|last4=Buchwald|first4=Stephen L.|journal=Journal of the American Chemical Society|volume=128|issue=33|pages=10694–10695|pmid=16910660}}</ref>
==References==
{{reflist}}

{{aromatic-stub}}

Category:Alkylphenols

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Adapted from the Wikipedia article [Mesitol](https://en.wikipedia.org/wiki/Mesitol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Mesitol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.