1,4-Cyclohexanedione → 2,3,9,10-Tetrachloro-6,13-pentacenequinone

HRID 1895570Notes

Reaction equation

HRID 1895570 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=O)[C:5]([CH:9]=O)=[CH:6][C:7]=1[Cl:8].[C:13]1(=[O:20])[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[C:4](=[CH:11][C:18]3[C:13](=[O:20])[C:14]4[C:15]([C:16](=[O:19])[C:17]=3[CH:9]=2)=[CH:11][C:4]2[C:5](=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:9]=4)[CH:3]=1

Participants

5

Reactant 3

HCID 125111,4-CyclohexanedioneHCID 14797Potassium HydroxideHCID 98371091,2-Benzenedicarboxaldehyde, 4,5-dichloro-

Product 1

HCID 582891062,3,9,10-Tetrachloro-6,13-pentacenequinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,5-Dichlorobenzene-1,2-dicarbaldehyde (2.0 g, 9.90 mmol) and 1,4-cyclohexanedione (0.62 g, 5.53 mmol) were stirred in 60 mL ethanol. To this was added dropwise with stirring, 10 mL of 5% aq potassium hydroxide. Upon addition of first drop, solution became black, brown, and then solids precipitate. Reaction mixture was stirred at RT for 1 h and refluxed for 2 h. Reaction mixture was cooled to RT, solids filtered, washed with water, dried to give 2,3,9,10-tetrachloro-6,13-pentacenequinone as brown solids in good yields (1.73 g, 70%). LDI-MS m/z: 446 [M+].

Workup

  1. additionTo this was added dropwise
  2. additionUpon addition of first drop, solution
  3. customReaction mixture
  4. stirringwas stirred at RT for 1 h
  5. temperaturerefluxed for 2 h
  6. customReaction mixture
  7. filtrationsolids filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-92aef89fec95429ea8495d0caa01b3d6
Source dataset
uspto-grants-2013_08
Patent number
US08513466B2

Reaction notes

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