(Phenanthren-4-yl)methanol → phenanthrene-4-carbaldehyde

HRID 1383035Notes

Reaction equation

HRID 1383035 reaction equation
[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([CH2:15][OH:16])=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([CH:15]=[O:16])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 89868(Phenanthren-4-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 299447phenanthrene-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Phenanthrenemethanol (Aldrich, 29 g, 0.14 mol) was treated with pyridinium chlorochromate (PCC) (Aldrich, 45 g, 0.21 mol) in CH2Cl2 (2000 mL). After 6 h at RT, the reaction mixture was filtered through a plug of SiO2 to give after removal of solvent and drying and crystallization from CH3OH, 20.5 g (71%) of phenanthrene-4-carboxaldehyde mp 82.5°-84.5° (C, H).

Workup

  1. filtrationthe reaction mixture was filtered through a plug of SiO2
  2. customto give
  3. customafter removal of solvent
  4. customdrying
  5. customcrystallization from CH3OH, 20.5 g (71%) of phenanthrene-4-carboxaldehyde mp 82.5°-84.5° (C, H)

Sources & evidence

ORD record
ord-cf539cb5c5bd43b6875ac9c8d2fc528f
Source dataset
uspto-grants-1989_02
Patent number
US04808625

Reaction notes

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