2-Anthracenemethanol → 2-anthracenecarbaldehyde

HRID 2413667Notes

Reaction equation

HRID 2413667 reaction equation
[CH:1]1[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][C:2]=1[CH2:15][OH:16].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:1]1[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][C:2]=1[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 12014782-AnthracenemethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 17123542-anthracenecarbaldehydeYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Antracenylmethanol (46A, 1.0 g, 0.0048 mol) in CH2Cl2 (700 mL) was treated with pyridinium chlorochromate (PCC) (Aldrich, 21.56 g, 0.1 mol) and heated for 4 h. The reaction was cooled and filtered through a plug of SiO2 (500 g) using CH2Cl2 as the eluting solvent. After removal of the solvent the crude material was chromatographed on SiO2 with PhCH3 as the eluting solvent to afford 0.5 g (51%) of 2-anthracenecarbaldehyde mp 201°-202.5° (lit mp 202°-203°, P. H. Gore, J. Chem. Soc. 1616 (1959)), (C, H).

Workup

  1. temperatureheated for 4 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through a plug of SiO2 (500 g)
  4. customAfter removal of the solvent the crude material
  5. customwas chromatographed on SiO2 with PhCH3 as the eluting solvent

Sources & evidence

ORD record
ord-9b625e896e4c4919ba26ed37956d4f76
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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