Orcinol synthesis

8synthesis methods

Product Name:Orcinol
CAS Number:504-15-4
Molecular formula:C7H8O2
Molecular Weight:124.14

Orcinol has been isolated from numerous lichen fungi (Robiquet, 1829) and can be synthesized by decarboxylation of orsellinic acid in Umbilicaria papulosa and Gliocladium roseum (Pettersson, 1965; Mosbach and Ehrensvard, 1966).
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. It can be obtained by fusing extract of aloes with potash, followed by acidification.
US3865884A: Preparation of orcinol

Benzene, 1-methyl-3,5-bis[(trimethylsilyl)oxy]-

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Yield:504-15-4 99%

Reaction Conditions:

with methanol;1,3-disulfonic acid imidazolium hydrogen sulfate at 20; for 0.1 h;Green chemistry;

Steps:

General procedure for the deprotection of trimethylsilyl ethers
General procedure: A mixture of the substrate (1 mmol), ionic liquid [Dsim]HSO4 (6.5 mg, ～0.02 mmol) in methanol (2 mL) was stirred at room temperature. After completion of the reaction (monitored by TLC), solvent was evaporated, water (1 mL) was added to the mixture, and stirred vigorously. Decantation of the mixture gave almost pure product(s). The products were characterized by comparison of their IR and NMR data. The ionic liquid was dried at 65 ?C under vacuum to remove moisture, and then reused.

References:

Shirini, Farhad;Khaligh, Nader Ghaffari;Akbari-Dadamahaleh, Somayeh [Journal of Molecular Catalysis A: Chemical,2012,vol. 365,p. 15 - 23]

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