2-Ethylanthraquinone → 2-Ethylanthracene
反応式
[CH2:1]([C:3]1[CH:16]=[CH:15][C:14]2[C:13](=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=O)[C:5]=2[CH:4]=1)[CH3:2].[NH4+].[OH-]>[Zn]>[CH2:1]([C:3]1[CH:16]=[CH:15][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]=1)[CH3:2]参加物
4
実験手順
To a 5 L 3-neck flask fitted with condenser, thermometer, and overhead stirrer was added 2-ethylanthraquinone (Aldrich, 120 g, 0.51 mmol), Zn dust (Mallinckrodt, 300 g, 4.59 mol), CuSO4.5H2O (Mallinckrodt, 3.0 g) and 28% NH4OH (Mallinckrodt, 2.8 mL). The temperature was increased until the initial dark red color had faded (about 6 h). The reaction mixture was then filtered. The filtrate was extracted with EtOAc (5×1 L), and the filter cake washed with EtOAc (2×1 L). The EtOAc solutions were combined and the solvent removed. The residue was refluxed with a mixture of conc. HCl (10 mL) in i-PrOH (1.2 L) for 2 h. Upon cooling, a solid precipitated which was filtered, washed with abs. EtOH (100 mL) and dried to give 40 g (38%) of 2-ethylanthracene mp 140°-142°, (lit. mp 148°-150°, L. H. Klemm et al., J. Org. Chem. 28, 625 (1983), (C, H).