Oxygen → 2,2'-Ethylenebis(3,6-dimethoxy1,4-benzoquinone)

Participants

Reaction Steps

Under ice-cooling conditions, 302 mg of 1,2-bis[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethanol was dissolved in 5 ml of trifluoroacetic acid, then 0.4 ml of triethylsilane was added to the solution. This mixture was stirred under ice-cooling conditions for 2 hours. After concentrated the reaction mixture, benzene was added and the mixture was further treated under a reduced pressure. The residue thus obtained was dissolved in 5 ml of methanol, and a catalytic amount of sodium hydrogen carbonate was added thereto, and oxygen gas was blown into the reaction mixture. 2 Hours later, the reaction mixture was filtered, and the filtrate was concentrated under a reduced pressure. The residue obtained was treated by means of a thin layer chromatography (adsorbent: silica gel, manufactured by E. Merck A. G., size: 20 cm×20 cm, thickness: 2 mm, 2 plates were used, developping solvent: 30% ethyl acetate-n-hexane) to obtain 132 mg of 2,2'-ethylenebis(3,6-dimethoxy1,4-benzoquinone). Yellow oily substance.

Provenance & Evidence