Mesitol

Mesitol
Names
Preferred IUPAC name
2,4,6-Trimethylphenol
Other names
Hydroxymesitylene; Mesityl alcohol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.655 Edit this at Wikidata
EC Number
  • 208-419-2
UNII
  • InChI=1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3
    Key: BPRYUXCVCCNUFE-UHFFFAOYSA-N
  • Cc1cc(c(c(c1)C)O)C
Properties
C9H12O
Molar mass 136.194 g·mol−1
Appearance white solid
Melting point 70–72 °C (158–162 °F; 343–345 K)[1]
Boiling point 220 °C (428 °F; 493 K)[1]
1.01 g/l
Hazards
GHS labelling:
GHS05: CorrosiveGHS09: Environmental hazard
Danger
H314, H411
P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[2]

It can also be obtained by reaction of mesitylene with peroxymonophosphoric acid:[3]

An alternative route involves palladium-catalyzed reaction of bromomesitylene with potassium hydroxide.[4]

References

  1. ^ a b "2,4,6-Trimethylphenol". Sigma-Aldrich.
  2. ^ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3527306730.
  3. ^ Ogata, Yoshiro; Sawaki, Yasuhiko; Tomizawa, Kohtaro; Ohno, Takashi (1981). "Aromatic hydroxylation with peroxymonophosphoric acid". Tetrahedron. 37 (8): 1485. doi:10.1016/S0040-4020(01)92087-3.
  4. ^ Anderson, Kevin W.; Ikawa, Takashi; Tundel, Rachel E.; Buchwald, Stephen L. (2006). "The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans". Journal of the American Chemical Society. 128 (33): 10694–10695. doi:10.1021/ja0639719. PMID 16910660.
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