Mesitol

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Mesitol
Mesitol V1.svg
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[edit]

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]

Peroxomonophosphoric acid reaction03.svg

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

References[edit]

  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 (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
  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.