Reaktion #1675337

Reaktionsgleichung

oxygen

hydrogen chloride

sodium hydrogen carbonate

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

→

2,2'-tetramethylenebis(3,6-dimethoxy-1,4 -benzoquinone)

Lösungsmittel

benzene

tetrahydrofuran isopropanol

methanol

isopropanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure, to the residue
3. 3
   Sonstigeobtained
4. 4
   Einengenfurther concentrated under reduced pressure
5. 5
   SonstigeThe residue thus obtained
6. 6
   Filtration2 Hours later, the reaction mixture was filtered
7. 7
   Einengenthe filtrate was concentrated under reduced pressure
8. 8
   Sonstigethe residue obtained
9. 9
   Sonstigewas purified by means of a silica gel chromatography (diameter 2 cm×length 5 cm, eluent: 30%-ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200")

Vorschrift

355 Milligrams of 2,2'-tetramethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene] was dissolved in a mixed solvent of 8 ml of isopropanol with 4 ml of tetrahydrofuran, to this solution was added 1.2 ml of solution prepared by dissolving 10% (by weight/weight) of hydrogen chloride in a mixed solvent of tetrahydrofuran-isopropanol (1:1), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, to the residue obtained was added benzene, and further concentrated under 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 thereinto. 2 Hours later, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure, and the residue obtained was purified by means of a silica gel chromatography (diameter 2 cm×length 5 cm, eluent: 30%-ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200") to obtain 120 mg of 2,2'-tetramethylenebis(3,6-dimethoxy-1,4 -benzoquinone). Yellow needles crystals.

Quelle