Hydrochloric Acid → 2-(3,6-Dimethoxy1,4-benzoquinon-2-yl)ethyl 3-(3,6-dimethoxy-1,4-benzoquinon2-yl)propyl ether

HRID 1588156ノート

反応式

HRID 1588156 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9]COC)=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15]COC)[C:4]=1[CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]1[C:30]([O:31][CH2:32]OC)=[C:29]([O:35]C)[CH:28]=[C:27]([O:37][CH2:38]OC)[C:26]=1[O:41]C.Cl.C(=O)([O-])O.[Na+].O=O>O1CCCC1.C(O)(C)C.CO.ClCCl>[CH3:1][O:2][C:3]1[C:8](=[O:9])[CH:7]=[C:6]([O:13][CH3:14])[C:5](=[O:15])[C:4]=1[CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]1[C:26](=[O:41])[C:27]([O:37][CH3:38])=[CH:28][C:29](=[O:35])[C:30]=1[O:31][CH3:32]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 516892Sodium BicarbonateHCID 197572532-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl ether

生成物 1

HCID 137145732-(3,6-Dimethoxy1,4-benzoquinon-2-yl)ethyl 3-(3,6-dimethoxy-1,4-benzoquinon2-yl)propyl ether

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 3776Isopropanol溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

484 Milligrams of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3-[2,5-dimethoxy-3,6bis(methoxymethoxy)phenyl]propyl ether was dissolved in a mixed solvent of 5 ml of tetrahydrofuran with 5 ml of isopropanol, to this solution was added 1.0 ml of solution prepared by dissolving 10% (by weight) of hydrogen chloride in a mixture of tetrahydrofuran with isopropanol (1:1), and the whole mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated, and benzene was added then further treated under reduced pressure to concentrated. The residue obtained was dissolved in 10 ml of methanol, and a catalytical amount of sodium hydrogen carbonate was added thereto and oxygen gas was blown thereinto. The precipitated crystals were dissolved by adding dichloromethane and filtered. The filtrate was concentrated and the residue obtained was purified by means of a silica gel column chromatography, (diameter 2 cm×length 5 cm, developping solvent: 10% ethyl acetate-dichloromethane solution, adsorbent: "Wakogel C-200", to obtain a crude product, then recrystallized from ethanol to obtain 243 mg of 2-(3,6-dimethoxy1,4-benzoquinon-2-yl)ethyl 3-(3,6-dimethoxy-1,4-benzoquinon2-yl)propyl ether. Yellow needles crystals.

後処理

  1. customprepared
  2. concentrationThe reaction mixture was concentrated
  3. additionbenzene was added
  4. additionthen further treated under reduced pressure
  5. concentrationto concentrated
  6. customThe residue obtained
  7. dissolutionThe precipitated crystals were dissolved
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customthe residue obtained
  11. customwas purified by means of a silica gel column chromatography
  12. custom10% ethyl acetate-dichloromethane solution, adsorbent: "Wakogel C-200", to obtain a crude product
  13. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-db3bf2ff02dc4fd4b1172206de50653d
出典データセット
uspto-grants-1993_06
特許番号
US05220042

反応ノート

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