2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Pyrene-4-carbaldehyde

HRID 620523Notes

Reaction equation

HRID 620523 reaction equation
[CH2:1]1[C:14]2[C:15]3[C:16]4[C:11](=[CH:12][CH:13]=2)[CH2:10][CH2:9][CH2:8][C:7]=4[CH:6]=[C:5]([CH:17]=[O:18])[C:4]=3[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[C:5]([CH:17]=[O:18])[C:4]3=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15050894HCID 15050894, compound

Product 1

HCID 186069Pyrene-4-carbaldehydeYield 77.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,6,7,8-Hexahydro-4-pyrenecarbaldehyde (19A, 11.81 g, 50 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (Aldrich, 39.75 g, 0.175 mol) were refluxed for 4 h in 1 L of PhCH3. The reaction mixture was cooled and then filtered. The filtrate was washed with 2N NaOH (3×500 mL), satd. NaCl solution (2×500 mL), dried (Na2SO4), and passed through a plug of SiO2 (200 g). The solvent was then removed to give a bright yellow solid that was dried at 50° to give 8.91 g (77%) of 4-pyrenecarbaldehyde which was used without further purification. An analytical sample had mp 172°-174°, (CH2Cl2 /hexane), (C, H), (lit. mp 177°-179°, Y. E. Gerasimenko and I. N. Shevcbuk, Zh. Org. Khim. 4 2198 (1968)).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with 2N NaOH (3×500 mL)
  4. dry with materialNaCl solution (2×500 mL), dried (Na2SO4)
  5. customThe solvent was then removed
  6. customto give a bright yellow solid
  7. customthat was dried at 50°

Sources & evidence

ORD record
ord-d14442923ef14cd5890e515f40aa4b9a
Source dataset
uspto-grants-1989_04
Patent number
US04820873

Reaction notes

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