Reaktion #1675319

Reaktionsgleichung

1,16-bis(5-methoxy-2-hydroxy-1,4-benzoquinon-3-yl)-8,9-epoxyhexadecane

perchloric acid

diethyl ether

→

1,16-bis(5-methoxy-2-hydroxy-1,4-benzoquinon-3-yl)-8,9-dihydroxyhexadecane

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe organic layer was washed with a saturated sodium chloride aqueous solution in several times
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   SonstigeThis extract was purified by means of a preparative thin layer chromatography [adsorbent: "Silica gel 60 F254 " manufactured by E. Merck A. G., developing solvent: chloroform-methanol (85:15 mixture by volume/volume)]
4. 4
   Sonstigerecrystallized from ethyl acetate-n-hexane

Vorschrift

37 Milligrams of 1,16-bis(5-methoxy-2-hydroxy-1,4-benzoquinon-3-yl)-8,9-epoxyhexadecane was dissolved in 2 ml of tetrahydrofuran, to this solution was added 0.5 ml of 5% perchloric acid aqueous solution and the mixture was stirred at room temperature for 4 hours. Then, 30 ml of diethyl ether was added to the reaction mixture, and the organic layer was washed with a saturated sodium chloride aqueous solution in several times, and dried over anhydrous sodium sulfate. This extract was purified by means of a preparative thin layer chromatography [adsorbent: "Silica gel 60 F254 " manufactured by E. Merck A. G., developing solvent: chloroform-methanol (85:15 mixture by volume/volume)], then recrystallized from ethyl acetate-n-hexane to obtain 12 mg of 1,16-bis(5-methoxy-2-hydroxy-1,4-benzoquinon-3-yl)-8,9-dihydroxyhexadecane. Yellow powdery crystals.

Quelle