(Anthracen-1-yl)methanol → Anthracenecarboxaldehyde

HRID 1381777Notes

Reaction equation

HRID 1381777 reaction equation
[C:1]1([CH2:15][OH:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH:15]=[O:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12695455(Anthracen-1-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 35864AnthracenecarboxaldehydeYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2 L round bottom flask equipped with condenser and magentic stirring bar was added (1-anthracenyl)methanol (15C, 21.0 g, 0.10 mol), CH2Cl2 (1200 mL) and pyridinium chlorochromate (PCC) (Aldrich, 32.33 g, 0.15 mol). The mixture was then refluxed for 5 h. The reaction was cooled and then filtered through a plug of silica gel (400 g) using PhCH3 as eluting solvent. The first 1 L of solution was collected and concentrated to give 16 g of crude product. This material was further purified by preparative HPLC using PhCH3 as eluting solvent. The solvent was removed and the resulting solid recrystallized (PhCH3 /hexane) to give 14.0 g (67%) of 1-anthracenecarbaldehyde mp 130°-131.5°, (C, H), (lit. mp 126.5°-127.5°, P. H. Gore J. Chem. Soc. 1616 (1959)).

Workup

  1. customTo a 2 L round bottom flask equipped with condenser and magentic stirring bar
  2. temperatureThe mixture was then refluxed for 5 h
  3. temperatureThe reaction was cooled
  4. filtrationfiltered through a plug of silica gel (400 g)
  5. washas eluting solvent
  6. customThe first 1 L of solution was collected
  7. concentrationconcentrated
  8. customto give 16 g of crude product
  9. customThis material was further purified by preparative HPLC
  10. washas eluting solvent
  11. customThe solvent was removed
  12. customthe resulting solid recrystallized (PhCH3 /hexane)

Sources & evidence

ORD record
ord-102135cd8b234d1691ab6a98fb2e4b97
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

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