2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl-1-fluoranthenecarboxylate

HRID 2255818Notes

Reaction equation

HRID 2255818 reaction equation
[CH:1]1([C:17]([O-:19])=[O:18])[CH:15]2[C:16]3[C:4](=[CH:5][CH:6]=[CH:7][C:8]=3[C:9]3[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:3][CH2:2]1.[C:20](C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH3:20][O:18][C:17]([C:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1)=[O:19]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 197386131,2,3,10b-Tetrahydro-1-fluoranthenecarboxylate

Product 1

HCID 15050895Methyl-1-fluoranthenecarboxylateYield 97.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a RB flask equipped with magnetic stirrer, condenser and N2 inlet line with bubbler was added methyl, 1,2,3,10b-tetrahydro-1-fluoranthenecarboxylate (Cambridge Chemical, Inc., 202 E. Smith Street, Milwaukee, Wis. 53207, 98.0 g, 0.372 mol), DDQ (Aldrich, 177.0 g, 0.781 mol) and dry PhCH3 (2 L). The reaction mixture was heated at 90° for 10 h, cooled, filtered and concentrated to a 500 mL volume. The crude material was purified on a plug of SiO2 (0.5 kg) using PhCH3 as the eluting solvent. The appropriate fractions were combined and concentrated by rotary evaporation to give a crude pale yellow solid which was recrystallized (CH2Cl2 /hexane), filtered and dried to give 94.5 g (96%) of methyl-1-fluoranthenecarboxylate mp 70°-71°, (C,H).

Workup

  1. customTo a RB flask equipped with magnetic stirrer, condenser and N2 inlet line with bubbler
  2. temperatureThe reaction mixture was heated at 90° for 10 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated to a 500 mL volume
  6. customThe crude material was purified on a plug of SiO2 (0.5 kg)
  7. concentrationconcentrated by rotary evaporation
  8. customto give a crude pale yellow solid which
  9. customwas recrystallized (CH2Cl2 /hexane)
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-b2ace1269dce408296ff2bbbf8c8994a
Source dataset
uspto-grants-1993_08
Patent number
US05241107

Reaction notes

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