3-Hydroxymethylchrysene → Chrysene-3-carbaldehyde

HRID 1762013

Reaction equation

HRID 1762013 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-6f6893ba44144dcea0df6714001bbb56
Source dataset
uspto-grants-1989_05
Patent number
US04829090

Linked notes

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