(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol → (5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone

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Reaction Steps

(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone was prepared analogously to (4-methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanone using (5-methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol (2.9 g, 8.2 mmol) and pyridinium chlorochromate (2.6 g, 12.2 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5) to afford (5-methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone (2.2 g, 76%) as a white solid: 1H NMR (CDCl3) δ 8.22 (d, J=9 Hz, 1H), 7.11-7.06 (dd, J=3, 9 Hz, 1H), 7.00 (s, 2H), 6.89 (d, J=2 Hz, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 3.82 (s, 6H); 13C NMR (CDCl3) δ 191.95, 164.01, 153.25, 143.37, 139.57, 138.57, 130.85, 126.93, 115.30, 113.49, 106.78, 60.93, 56.32, 56.25.

Provenance & Evidence