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

HRID 444402Notes

Reaction equation

HRID 444402 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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 recrystallization 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.

Workup

  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 recrystallization from diethyl ether/tetrahydrofuran/methylene chloride (4:1:2) there

Sources & evidence

ORD record
ord-ac066600761544b5bfb102d7d3b58451
Source dataset
uspto-grants-1981_04
Patent number
US04264510

Reaction notes

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