反应详情

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)).

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)