2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 9842206, compound

HRID 1872099Notes

Reaction equation

HRID 1872099 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH2:10][CH2:9][C:8]=2[C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1C=CC=CC=1>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH:10]=[CH:9][C:8]=2[C:19](=[O:28])[C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18690204HCID 18690204, compound

Product 1

HCID 9842206HCID 9842206, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 11.1 g (30 mmol) of 1-phenyl-2-(4-methoxybenzoyl)-3,4-dihydro-6-methoxynaphthalene dissolved in benzene was added DDQ (9 g, 40 mmol). The mixture was heated to reflux for two hours and filtered while hot through silica gel. The silica gel was washed three times with ethyl acetate. The ethyl acetate washings and the benzene solution were combined and evaporated to dryness. The residue was crystallized from hot methanol, which yielded 4.5 g of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for two hours
  3. filtrationfiltered while hot through silica gel
  4. washThe silica gel was washed three times with ethyl acetate
  5. customevaporated to dryness
  6. customThe residue was crystallized from hot methanol, which

Sources & evidence

ORD record
ord-57476fefcd474417a714cf553f9ed463
Source dataset
uspto-grants-2000_08
Patent number
US06107346

Reaction notes

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