Acetic Acid → 3,3'-Dicarboxychalcone

Participants

Reaction Steps

A solution of 3,3′-dicyanochalcone from step 1 (2.0 g, 7.75 mmol) in glacial acetic acid (30 mL) was treated with a mixture of concentrated H2SO4 (10 mL) and water (10 mL). The reaction mixture was heated to 130 C for 12 hours, cooled to room temperature and filtered. The precipitate was washed with water (3×100 mL) and dried in vacuo to give 3,3′-dicarboxychalcone as a yellow solid. MS (APCI) m/z 295 (M+−1, 100%). 13C NMR (50 MHz, d6-DMSO); δ 122.5, 128.6, 128.7, 129.2, 130.8, 131.0, 131.2, 132.4, 132.5, 133.1, 134.5, 137.2, 143.1, 166.3, 166.5, 188.2

Provenance & Evidence