反应详情

To a 5 L 3-neck flask fitted with condenser, thermometer, and overhead stirrer was added 9,10-dihydro-9,10-dioxo-1-anthracenecarboxylic acid (15A, 90 g, 0.357 mol), Zn dust (Mallinckrodt, 250 g, 3.82 mol), CuSO4.5H2O (Mallinckrodt, 5 g) and 28% NH4OH (Mallinckrodt, 2500 mL). The mixture was heated slowly. A dark-red solution occurred as the temperature reached 85°. After 3.5 h, the color of the solution faded to yellow. The reaction was heated an additional 1 h, cooled and the excess Zn removed by filtration. The filter cake was washed with more NH4OH solution (100 mL) and then discarded. The filtrate was carefully acidified to pH 1 with conc. HCl (added in portions over 1 h) affording a light-green precipitate, which was separated by filtration. The solid was washed with H2O (200 mL) and then recrystallized 1× from methoxyethanol/H2O (containing 1% conc. HCl), filtered and dried at 75°, to give 65 g (82%) of 1-anthracenecarboxylic acid mp 249°-250°, (C, H), (lit. mp 245°, Chemistry of Carbon Compounds IIIb, edited by E. H. Rodd, 1373 (1956), Elsevier, N.Y.).

1. customTo a 5 L 3-neck flask fitted with condenser
2. temperatureThe mixture was heated slowly
3. customreached 85°
4. temperatureThe reaction was heated an additional 1 h
5. temperaturecooled
6. customthe excess Zn removed by filtration
7. washThe filter cake was washed with more NH4OH solution (100 mL)
8. customwas carefully acidified to pH 1 with conc. HCl (added in portions over 1 h)
9. customaffording a light-green precipitate, which
10. customwas separated by filtration
11. washThe solid was washed with H2O (200 mL)
12. customrecrystallized 1× from methoxyethanol/H2O (containing 1% conc. HCl)
13. filtrationfiltered
14. customdried at 75°