3,4,5-Trimethoxyphenol → 2'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalcone

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A mixture of 3,4,5-trimethoxyphenol (1.85 g, 10 mmol) and 4-nitrocinnamoyl chloride (2.11 g, 10 mmol) was dissolved in BF3-Et2O complex (10 ml) and heated to 80° C. for 10 min, and then quenched with excess of water. The aqueous layer was extracted with dichloromethane. The combined organic layer was concentrated and the residue was purified by column chromatography on silica gel (CH2Cl2:EtOAc:Hexane=1:1:3) gave 7a (0.79 g, 22%) and 7b (1.54 g, 43%). 1H NMR (400 MHz, CDCl3) μ 3.81 (s, 3H), 3.90 (s, 3H), 3.91 (s, 3H), 6.29 (s, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.76 (d, J=16.0 Hz, 1H), 8.01 (d, J=16.0 Hz, 1H), 8.26 (d, J=8.8 Hz, 2H), 13.44 (s, 1H).

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