2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 18976134, compound

HRID 2393518Notes

Reaction equation

HRID 2393518 reaction equation
[CH2:1]1[C:6]2=[C:7]3[CH:16]([CH:17]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[CH:5]2[CH2:4][CH2:3][CH2:2]1)[O:15][C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[O:8]3.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH:1]1[C:6]2[C:7]3[O:8][C:9]4[C:14]([O:15][C:16]=3[CH:17]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:13][CH:12]=[CH:11][CH:10]=4

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18976127HCID 18976127, compound

Product 1

HCID 18976134HCID 18976134, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an inert atmosphere, 370 mg of methyl 1,2,3,4,4a,6a-hexahydro-7,12-dioxabenz[a]anthracene-5-carboxylate in solution in 10 ml of toluene are brought to reflux for 6 hours in the presence of 986 mg of DDQ. After cooling, the reaction mixture is washed with 8% sodium hydroxide solution. The organic phase is dried over magnesium sulfate and then concentrated under vacuum. Purification is performed by chromatography on silica gel (eluent: petroleum ether/ethyl acetate, 95:5).

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture is washed with 8% sodium hydroxide solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customPurification

Sources & evidence

ORD record
ord-66164cb2d8934eb682aa37d588efd992
Source dataset
uspto-grants-1998_09
Patent number
US05807882

Reaction notes

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