mesitol
{{Chembox
|ImageFile = Mesitol_V1.svg
|ImageSize = 150px
|PIN = 2,4,6-Trimethylphenol
|OtherNames = Hydroxymesitylene; Mesityl alcohol
|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 = {{cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/w432900 | publisher = Sigma-Aldrich | title = 2,4,6-Trimethylphenol }}
|BoilingPtC = 220
|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 with the formula (CH3)3C6H2OH. It is one of several isomers of trimethylphenol. The name and structure of mesitol derives from the combination of mesitylene and phenol.
Synthesis
Mesitol is the main product from the methylation of phenol with methanol in the presence of a solid acid.{{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}}
It can also be obtained by reaction of mesitylene with peroxymonophosphoric acid:{{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}}
:File:Peroxomonophosphoric_acid_reaction03.svg{{clear-left}}
An alternative route involves palladium-catalyzed reaction of bromomesitylene with potassium hydroxide.{{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}}