Orcinol

Source: Wikipedia, the free encyclopedia.
Orcinol[1]
Names
Preferred IUPAC name
5-Methylbenzene-1,3-diol
Other names
  • 5-Methylresorcinol
  • 3,5-Toluenediol
  • Orcin
  • 5-Methyl-1,3-benzenediol
  • 3,5-Dihydroxytoluene
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.259 Edit this at Wikidata
UNII
  • InChI=1S/C7H8O2/c1-5-2-6(8)4-7(9)3-5/h2-4,8-9H,1H3
    Key: OIPPWFOQEKKFEE-UHFFFAOYSA-N
  • CC1=CC(=CC(=C1)O)O
Properties
C7H8O2
Molar mass 124.139 g·mol−1
Appearance Crystalline solid
Melting point 109.0 °C (228.2 °F; 382.1 K)[2]
Boiling point 291 °C (556 °F; 564 K)[2]
Miscible
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Orcinol is an organic compound with the formula CH3C6H3(OH)2. It occurs in many species of

Camponotus saundersi. It is a colorless solid. It is related to resorcinol
, 1,3-C6H4(OH)2.

Synthesis and reactions

Orcinol was first prepared by dehydroacetic acid, a conversion that involved ring-opening of the pyrone to a triketone. This early experiment helped establish the rich condensation chemistry of polyketides.[4] It can be obtained by fusing extract of aloes with potash,[5] followed by acidification.

It undergoes O-

dimethylsulfate.[6]

It is used in the production of the dye

Ferric chloride gives a bluish-violet coloration with the aqueous solution. Unlike resorcinol it does not give a fluorescein with phthalic anhydride. Oxidation of the ammoniacal solution gives orcein, C28H24N2O7, the chief constituent of the natural dye archil. 4-Methylcatechol is an isomer, found as its methyl ether (creosol) in beech-wood tar.[5]

Orcinol

Production from shale oil

Orcinol is also found in shale oil produced from Kukersite oil shale.[2] It is the main water-soluble phenol in the oil, and has been extracted and refined industrially by Viru Keemia Grupp.[7]

See also

References

  1. ^ Merck Index, 11th Edition, 6819.
  2. ^
    ISSN 0021-9568
    .
  3. ^ Robiquet: „Essai analytique des lichens de l'orseille", Annales de chimie et de physique, 1829, 42, p. 236–257.
  4. PMID 11548049
    .
  5. ^ a b  One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Orcin". Encyclopædia Britannica. Vol. 20 (11th ed.). Cambridge University Press. p. 173.
  6. doi:10.15227/orgsyn.053.0090
    .
  7. ^ "Fine chemicals". Viru Keemia Grupp. Retrieved 2020-10-23.
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