2-Anthracenemethanol → 2-anthracenecarbaldehyde

HRID 1381804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381804
[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]

Komponenten

4

Edukt 2

HCID 12014782-AnthracenemethanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 17123542-anthracenecarbaldehydeAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Anthracenylmethanol (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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-90eee7970e444c2380bb5eff494f78f6
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803221

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