2-Ethylanthraquinone → 2-Ethylanthracene

To a 5 L 3-neck flask fitted with condenser, thermometer, and overhead stirrer was added 2-ethylanthraquinone (Aldrich, 120 g, 0.51 mol), 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).

1. customTo a 5 L 3-neck flask fitted with condenser
2. temperatureThe temperature was increased until the initial dark red color
3. custom(about 6 h)
4. filtrationThe reaction mixture was then filtered
5. extractionThe filtrate was extracted with EtOAc (5×1 L)
6. washthe filter cake washed with EtOAc (2×1 L)
7. customthe solvent removed
8. temperatureThe residue was refluxed with a mixture of conc. HCl (10 mL) in i-PrOH (1.2 L) for 2 h
9. temperatureUpon cooling
10. customa solid precipitated which
11. filtrationwas filtered
12. washwashed with abs
13. dry with materialEtOH (100 mL) and dried

ORD record

ord-f54d7ae5f3d04513abb2af18cc9f2a5e

Source dataset

uspto-grants-1988_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04719049