2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,2,3,4-Tetrahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthracene

HRID 1154770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1154770
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]2[C:4]=1[CH2:5][C:6]1[CH:7]3[O:19][CH:10]([C:11]=1[CH2:12]2)[C:9](=[CH2:20])[C:8]3=[CH2:21].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]2[C:4]=1[CH:5]=[C:6]1[C:11](=[CH:12]2)[CH:10]2[O:19][CH:7]1[C:8](=[CH2:21])[C:9]2=[CH2:20]

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 133409781,2,3,4,9,10-Hexahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthracene

Produkt 1

HCID 126711181,2,3,4-Tetrahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthraceneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 2 g (7.1 mmol) of 1,2,3,4,9,10-hexahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthracene, 1.77 g (7.8 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 30 ml of benzene was stirred at room temperature under nitrogen for 30 minutes. The precipitate formed was filtered off and washed with benzene, the benzene solution was washed with two 30 ml portions of saturated aqueous sodium hydrogen sulphite solution and two 30 ml portions of water, dried over sodium sulphate and concentrated to dryness. By recrystallisation from diethyl ether/tetrahydrofuran/methylene chloride (4:1:2) there were obtained 1.95 g (98%) of 1,2,3,4-tetrahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthracene of melting point 205°-206° C. in the form of white crystals.

Aufarbeitung

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with benzene
  4. washthe benzene solution was washed with two 30 ml portions of saturated aqueous sodium hydrogen sulphite solution and two 30 ml portions of water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness
  7. customBy recrystallisation from diethyl ether/tetrahydrofuran/methylene chloride (4:1:2) there

Quellen und Nachweise

ORD-Eintrag
ord-8c60cba2c9e943f3929e6cc57aa1c3c0
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04298535

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