3-Hydroxymethylchrysene → Chrysene-3-carbaldehyde

HRID 2413599Notes

Reaction equation

HRID 2413599 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[CH:8][C:9]3[C:18]([C:19]=2[CH:20]=1)=[CH:17][CH:16]=[C:15]1[C:10]=3[CH:11]=[CH:12][CH:13]=[CH:14]1>C(Cl)Cl>[CH:5]1[C:6]2[CH:7]=[CH:8][C:9]3[C:18](=[CH:17][CH:16]=[C:15]4[C:10]=3[CH:11]=[CH:12][CH:13]=[CH:14]4)[C:19]=2[CH:20]=[C:3]([CH:2]=[O:1])[CH:4]=1

Participants

3

Reactant 1

HCID 155993273-Hydroxymethylchrysene

Product 1

HCID 15599326Chrysene-3-carbaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxymethylchrysene (19F, 14.6 g, 0.057 mol) in CH2Cl2 (2 L) was treated with BaMnO4 (Aldrich, 29 g, 0.113 mol) and refluxed for 15 h. The reaction mixture was filtered, the solvent removed, and the resulting solid eluted through a plug of SiO2 (500 g) using PhCH3 as the eluting solvent. The appropriate fractions were combined and concentrated to 75 mL. Filtration and drying of the precipitate which formed gave 12.88 g (89%) of chrysene-3-carbaldehyde mp 177°-177.5°, (C,H).

Workup

  1. temperaturerefluxed for 15 h
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent removed
  4. washthe resulting solid eluted through a plug of SiO2 (500 g)
  5. concentrationconcentrated to 75 mL
  6. filtrationFiltration
  7. customdrying of the precipitate which
  8. customformed

Sources & evidence

ORD record
ord-b80d862f5a914bb4a3bd0bd60efb5283
Source dataset
uspto-grants-1988_01
Patent number
US04719048

Reaction notes

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