Reaktion #1675325

Reaktionsgleichung

oxygen

1-[2,5-dimethoxy-4-butyl-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane

hydrogen chloride

sodium hydrogen carbonate

→

1-(2,5-dimethoxy-6-butyl-1,4-benzoquinone-3-yl)-5-[2,5-dimethoxy-6-(2-hydroxyethyl)-1,4-benzoquinon- 3-yl]pentane

Lösungsmittel

methanol

tetrahydrofuran

isopropanol

benzene

tetrahydrofuran isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentrated the reaction mixture
2. 2
   Sonstigethe residue obtained
3. 3
   EinengenThis solution was concentrated
4. 4
   workup.ADDITION50 ml of dichloromethane was added to the residue
5. 5
   Waschenthe solution was washed with water and with a saturated sodium chloride aqueous solution
6. 6
   Einengenconcentrated
7. 7
   SonstigeThen this product was purified by means column chromatography (diameter 2 cm×length 10 cm, adsorbent

Vorschrift

520 Milligrams of 1-[2,5-dimethoxy-4-butyl-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane was dissolved in 5 ml of tetrahydrofuran with 5 ml of isopropanol, to this solution was added 1 milliliter of tetrahydrofuran-isopropanol (1:1) solution of 20%-hydrogen chloride, and the whole mixture was stirred at room temperature for 12 hours. After concentrated the reaction mixture, the residue obtained was treated by an azeotrotic distillation with benzene, then dissolved in 8 ml of methanol, further a small amount of sodium hydrogen carbonate was added thereto, and oxygen gas was blown into the solution for 2 hours. This solution was concentrated, and 50 ml of dichloromethane was added to the residue and the solution was washed with water and with a saturated sodium chloride aqueous solution, and concentrated. Then this product was purified by means column chromatography (diameter 2 cm×length 10 cm, adsorbent: "Silica gel 60" manufacture by E. Merck A. G., developing solvent: 30% ethyl acetate-n-hexane) to obtain 231 mg of 1-(2,5-dimethoxy-6-butyl-1,4-benzoquinone-3-yl)-5-[2,5-dimethoxy-6-(2-hydroxyethyl)-1,4-benzoquinon- 3-yl]pentane. Amorphous powdery substance.

Quelle