Water → 4-Hydroxy-3,5-dimethoxybenzyl 4-hydroxyphenyl thioether

HRID 357709

Reaktionsgleichung

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18]C)=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][CH:3]=1.O>C(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([OH:18])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

3,4,5-Trimethoxybenzyl 4-hydroxyphenyl thioether (3 g, 9.8 mmol), prepared as described in Example 1, was dissolved in 60 ml of dry methylene chloride, and cooled to -78° C. A solution of borontribromide (2.8 ml, 29.5 mmol) in 10 ml of methylene chloride was added dropwise to the above solution. The mixture was stirred to room temperature, and immediately cooled to 0° C. Water (50 ml) was then added dropwise, and the methylene chloride layer was separated. The crude product, obtained after being dried over magnesium sulfate and concentrated, was purified on silica gel column chromatography (ethyl acetate/n-hexane=1/2) to give 1.8 g (63% yield) of 4-hydroxy-3,5-dimethoxybenzyl 4-hydroxyphenyl thioether as a white solid.

Aufarbeitung

temperatureimmediately cooled to 0° C
customthe methylene chloride layer was separated
customThe crude product, obtained
dry with materialafter being dried over magnesium sulfate
concentrationconcentrated
customwas purified on silica gel column chromatography (ethyl acetate/n-hexane=1/2)

Quellen und Nachweise

ORD-Eintrag: ord-452f5651b20a4cdf9b9505d7bd5ee1a0
Quelldatensatz: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05840991

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