tert-Butanol → 4,6-Di-tert-butyl-5-hydroxy-2-methylbenzofuran

HRID 1452371Notizen

Reaktionsgleichung

CS(O)(=O)=O.[C:6]([C:10]1[C:15]2[CH:16]=[C:17]([CH3:19])[O:18][C:14]=2[CH:13]=[CH:12][C:11]=1[OH:20])([CH3:9])([CH3:8])[CH3:7].[C:21](O)([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:6]([C:10]1[C:15]2[CH:16]=[C:17]([CH3:19])[O:18][C:14]=2[CH:13]=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]=1[OH:20])([CH3:9])([CH3:8])[CH3:7]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Methanesulfonic acid (1.2 ml) was added dropwise to a chloroform solution of 4-tert-butyl-5-hydroxy-2-methylbenzofuran (250 mg, 1.2 mmol) and tert-butyl alcohol (500 mg, 6.0 mmol) under cooling with ice. After stirring at 0° C. for 15 min, the mixture was poured into ice water. The mixture was then neutralized with 1N aqueous sodium hydroxide and subjected to extraction with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (n-hexane) to afford 4,6-di-tert-butyl-5-hydroxy-2-methylbenzofuran (35 mg) as a pale yellow oil.

Aufarbeitung

temperatureunder cooling with ice
extractionsubjected to extraction with ethyl acetate
washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe concentrate was purified by silica gel chromatography (n-hexane)

Quellen und Nachweise

ORD-Eintrag: ord-c2fcfb8fbeff4cc396dc08ad4c8649f5
Quelldatensatz: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05606089

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