2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14371436, compound

HRID 414402Notes

Reaction equation

HRID 414402 reaction equation
[CH:1]1[C:6]2[C:7]3[C:16]([CH2:17][CH2:18][C:5]=2[CH:4]=[C:3]([CH:19]=[O:20])[CH:2]=1)=[CH:15][C:14]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=1[CH:8]=3.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH:1]1[C:6]2=[C:7]3[C:16](=[CH:17][CH:18]=[C:5]2[CH:4]=[C:3]([CH:19]=[O:20])[CH:2]=1)[CH:15]=[C:14]1[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]1)=[CH:8]3

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14371437HCID 14371437, compound

Product 1

HCID 14371436HCID 14371436, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a RB flask equipped with magnetic stirring bar, reflux condenser and N2 inlet line with bubbler added 5,6,8,9,10,11-hexahydrobenz[a]anthracene-3-carbaldehyde (7A, 10.41 g, 39.7 mmol), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (Aldrich, 27.02 g, 0.119 mol) and dry PhCH3 (500 mL). The mixture was refluxed for 2 h until no more starting material remained by TLC, cooled and filtered to give a deep red solution. The solution was applied to a 40×10 cm column of SiO2 and eluted with additional PhCH3 as the solvent. The appropriate fractions were combined and the solvent removed to give 6.01 g of crude material. This was crystallized twice from PhCH3 /hexane (1:4) and dried to give 2.94 g (28.9% yield) of benz[a]anthracene-3-carbaldehyde, mp 144°-145°, (C, H).

Workup

  1. customTo a RB flask equipped with magnetic stirring bar
  2. temperaturereflux condenser and N2 inlet line with bubbler
  3. temperatureThe mixture was refluxed for 2 h until
  4. temperaturecooled
  5. filtrationfiltered
  6. customto give a deep red solution
  7. washeluted with additional PhCH3 as the solvent
  8. customthe solvent removed
  9. customto give 6.01 g of crude material
  10. customThis was crystallized twice from PhCH3 /hexane (1:4)
  11. customdried

Sources & evidence

ORD record
ord-3a6a4b7acbe04b06bafd04960469e2a1
Source dataset
uspto-grants-1988_12
Patent number
US04791232

Reaction notes

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