Guaiacol

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Guaiacol
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IUPAC name 2-methoxyphenol
Identifiers
CAS number 90-05-1
PubChem 460
SMILES COC1=CC=CC=C1O
Properties
Molecular formula C7H8O2
Molar mass 124.137
Density (Liquid)1.112 g/cm3(Crystals)1.129 g/cm3
Melting point

28 °C

Boiling point

204-206 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Guaiacol is a naturally occurring organic compound with the formula C6H4(OH)(OCH3). This colourless aromatic oil is derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke, resulting from the pyrolysis of lignin.

Preparation

Guaiacol is synthesized by the di-methylation of catechol followed by selective mono-demethylation.[1]

C6H4(OH)2 + 2 (CH3O)2SO2 → C6H4(OCH3)2 + 2 HO(CH3O)SO2
C6H4(OCH3)2 + C2H5SNa → C6H4(OCH3)(OH)

Uses

Guaiacol is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is also used in the preparation of eugenol[2] and vanillin[3].

References

  1. R. N. Mirrington and G. I. Feutrill “Orcinol Monomethyl Ether” Organic Syntheses, Collected Volume 6, p.859 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0859.pdf
  2. C. F. H. Allen and J. W. Gates, Jr. “o-Eugenol” Organic Syntheses, Collected Volume 3, p.418 (1955).http://www.orgsyn.org/orgsyn/pdfs/CV3P0418.pdf
  3. Esposito, Lawrence J.; K. Formanek, G. Kientz, F. Mauger, V. Maureaux, G. Robert, and F. Truchet (1997). "Vanillin". Kirk-Othmer Encyclopedia of Chemical Technology, 4th edition 24. New York: John Wiley & Sons. 812–825. 

See also

it:Guaiacolo


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