(Anthracen-1-yl)methanol → Anthracenecarboxaldehyde

Participants

Reaction Steps

To a 2 L round bottom flask equipped with condenser and magnetic stirring bar was added (1-anthryl)methanol (21.0 g, 0.10 mol), CH2Cl2 (1200 mL) and pyridinium chlorochromate (Aldrich, 32.33 g, 0.15 mol). The mixture was then refluxed for 5 h. The reaction was cooled and then filtered through 400 g plug of silica gel 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 purified by preparative HPLC using PhCH3 as eluting solvent. The solvent was removed and the pure material recrystallized from 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)).

Provenance & Evidence