2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 20563340, compound

HRID 1154777Notes

Reaction equation

HRID 1154777 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]=[C:16]1[C:29](=[CH2:30])[CH:28]2[O:31][CH:17]1[C:18]1[CH2:19][C:20]3[C:25]([CH2:26][C:27]=12)=[C:24]([O:32][CH3:33])[CH:23]=[CH:22][CH:21]=3>C1C=CC=CC=1>[CH2:15]=[C:16]1[C:29](=[CH2:30])[CH:28]2[O:31][CH:17]1[C:18]1[C:27]2=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[O:32][CH3:33])[CH:19]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13373178HCID 13373178, compound

Product 1

HCID 20563340HCID 20563340, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.24 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone were added at room temperature under a nitrogen atmosphere to a solution of 1.56 g of crude 1,2,3,4,9,10-hexahydro-2,3-dimethylene-1,4-epoxy-5-methoxyanthracene in 50 ml of benzene. After 1 hour, the suspension was filtered and the filtrate was washed with benzene. The organic solution was washed with two 75 ml portions of sodium hydrogen sulphite solution and two 75 ml portions of water. The aqueous phase was extracted with 50 ml of benzene and the combined organic solutions were dried over magnesium sulphate. After concentration, the residue was dissolved in 150 ml of diethyl ether, the solution was stirred with active carbon, the mixture was filtered and subsequently the filtrate was concentrated. Crystallisation of the residue from methanol yielded 1.09 g (70%) of 1,2,3,4-tetrahydro-2,3-dimethylene-1,4-epoxy-5-methoxyanthracene of melting point 154°-155° C.

Workup

  1. filtrationthe suspension was filtered
  2. washthe filtrate was washed with benzene
  3. washThe organic solution was washed with two 75 ml portions of sodium hydrogen sulphite solution and two 75 ml portions of water
  4. extractionThe aqueous phase was extracted with 50 ml of benzene
  5. dry with materialthe combined organic solutions were dried over magnesium sulphate
  6. concentrationAfter concentration
  7. dissolutionthe residue was dissolved in 150 ml of diethyl ether
  8. filtrationthe mixture was filtered
  9. concentrationsubsequently the filtrate was concentrated
  10. customCrystallisation of the residue from methanol

Sources & evidence

ORD record
ord-cce55fe17d4645528cd15cfe1501c4c6
Source dataset
uspto-grants-1981_11
Patent number
US04298535

Reaction notes

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