3-Methoxyphenol → 4-Tert-butyl-3-methoxyphenol

HRID 1350818

Reaktionsgleichung

[C:1](OC)([CH3:4])([CH3:3])[CH3:2].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[C:1]([C:14]1[CH:13]=[CH:12][C:11]([OH:15])=[CH:10][C:9]=1[O:8][CH3:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a suspension of zirconium tetrachloride (2.3 g, 10 mmol) in methylene dichloride (30 ml) was added methyl tert-butyl ether (0.88 g, 10 mmol) at 0° C. After stirring at 0° C. for 30 minutes, 3-methoxyphenol (1.24 g, 10 mmol) in methylene dichloride was added and the mixture was stirred for 2 hours at ambient temperature. The reaction was quenched with saturated aqueous sodium bicarbonate, followed by the addition of methylene dichloride. Then, the organic layer was separated, dried over magnesium sulfate, filtered off, evaporated under reduced pressure to give a residue, which was applied to a silica gel chromatography column eluted with a volume mixture of hexane and ethylacetate (20/1 to 4/1) to furnish 360 mg (20% yield) of the title compound as a white solid.

Aufarbeitung

stirringthe mixture was stirred for 2 hours at ambient temperature
customThe reaction was quenched with saturated aqueous sodium bicarbonate
additionfollowed by the addition of methylene dichloride
customThen, the organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered off
customevaporated under reduced pressure
customto give a residue, which
washeluted with a volume mixture of hexane and ethylacetate (20/1 to 4/1)

Quellen und Nachweise

ORD-Eintrag: ord-aee84e76d0484b708a5c56fffb3a1794
Quelldatensatz: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07214824B2

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