Reaktion #1675339

Reaktionsgleichung

oxygen

hydrogen chloride

2,2'-trimethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene]

sodium hydrogen carbonate

→

2,2'-trimethylenebis(3,6-dimethoxy1,4-benzoquinone)

Lösungsmittel

isopropanol

methanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed by evaporation under reduced pressure
2. 2
   Sonstigethe residue obtained
3. 3
   SonstigeThe solvent was removed by evaporation
4. 4
   workup.ADDITIONthe resulting residue was treated by means on a preparative thin layer chromatography (thickness 1 mm, adsorbent
5. 5
   Sonstigeto obtain 50 mg of crude product
6. 6
   SonstigeThe crude product was recrystallized from ethanol

Vorschrift

169 Milligrams of 2,2'-trimethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene] was dissolved in 2 ml of tetrahydrofuran and 2 ml of isopropanol, then to this solution was added 0.4 ml of a tetrahydrofuranisopropanol (1:1) solution containing 20% (by weight) of hydrogen chloride, then the mixture was stirred at room temperature for 1 day under argon gas stream condition. The solvent was removed by evaporation under reduced pressure, then the residue obtained was dissolved in 20 ml of methanol, and a small amount of sodium hydrogen carbonate was added to this solution, and stirred at room temperature for 30 minutes with blowing oxygen gas thereinto. The solvent was removed by evaporation, the resulting residue was treated by means on a preparative thin layer chromatography (thickness 1 mm, adsorbent: silica gel), and developped with a mixed solvent of ethyl acetate-n-hexane (1:1) to obtain 50 mg of crude product. The crude product was recrystallized from ethanol to obtain 20.4 mg of 2,2'-trimethylenebis(3,6-dimethoxy1,4-benzoquinone). Yellow fine needles crystals.

Quelle