Hydrochloric Acid → 3-(2,4-Dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

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Reaction Steps

A solution of 7 (3.2 g, 9.6 mmol) in triethylorthoformate (40 mL) and morpholine (10 mL) was heated to 120° C. for 4 hr. The reaction was allowed to cool to rt, poured into 2 N HCl and extracted with CH2Cl2. The CH2Cl2 was dried over MgSO4, concentrated and chromatographed on SiO2 (2:98 MeOH/CH2Cl2 to 4:96 (MeOH/CH2Cl2)) to give a the product 8 (1.5 g): Mp 202-204° C.; 1H NMR (CDCl3) δ 7.73 (s, 1H), 7.23 (d, 1H, J=9.0 Hz), 6.54-6.51 (m, 2H), 6.44 (d, 1H, J=2.3 Hz), 6.36 (d, 1H, J=2.3 Hz), 3.91 (s, 3H), 3.89 (s, 3H), 3.83 (s, 3H), 3.75 (s, 3H); MS FI 343 (M+H)+.

Provenance & Evidence