Reaktion #1675323

Reaktionsgleichung

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

tetrahydrofuran isopropanol

hydrogen chloride

→

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

Lösungsmittel

tetrahydrofuran

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentrated the reaction mixture
2. 2
   workup.ADDITIONthe residue was treated by an azeotropic distillation with benzene
3. 3
   workup.DISSOLUTIONdissolved in 8 ml of methanol
4. 4
   workup.ADDITIONfurther a small amount of sodium hydrogen carbonate was added
5. 5
   Einengen2 Hours later, the solution was concentrated
6. 6
   workup.ADDITION50 ml of dichloromethane was added
7. 7
   Waschenwashed with water
8. 8
   Trocknena saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
9. 9
   EinengenAfter concentrated
10. 10
    Sonstigethe residue was recrystallized from diethyl ether

Vorschrift

503 Milligrams of 1-[2,4,5-trimethoxy-3,6-bis(methoxymethoxy)phenyl]-5-[ 2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane was dissolved in a mixed solvent of 5 ml of tetrahydrofuran with 5 ml of isopropanol, to this solution was added 1 millilter of tetrahydrofuran-isopropanol (1:1) solution of 20%-hydrogen chloride, and the whole mixture was stirred for 12 hours. After concentrated the reaction mixture, the residue was treated by an azeotropic 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. 2 Hours later, the solution was concentrated, and 50 ml of dichloromethane was added, then washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After concentrated, the residue was recrystallized from diethyl ether to obtain 123 mg of 2-(2,5,6-trimethoxy)-1,4-benzoquinon-3-yl)-5-[2,5-dimethoxy-6(2-hydroxyethyl)-1,4-benzoquinon-3-yl]pentane. Yellow crystals.

Quelle