Water → 3,3'-Dicyanochalcone

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[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].[CH3:11][C:12]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][CH:15]=1)=O.OS(O)(=O)=O.O>C(O)(=O)C>[C:20]([C:18]1[CH:19]=[C:14]([CH:12]=[CH:11][C:6]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:7])[CH:15]=[CH:16][CH:17]=1)#[N:21]

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실험 절차

3-Cyanobenzaldehyde (3.0 g, 23.0 mmol) and 3-cyanoacetophenone (3.34 g, 23.0 mmol) in glacial acetic acid (5 mL) and concentrated H2SO4 (3.66 mL, 69 mmol) was stirred at room temperature for 72 hours. Water (200 mL) was added and the reaction filtered. The precipitate was washed with water (2×200 mL) and dried in vacuo to give 3,3′-dicyanochalcone as an off-white solid. MS (APCI) m/z 258 (M+−1, 100%). 13C NMR (50 MHz, d6-DMSO): δ111.7, 117.8, 118.0, 123.0, 129.7, 131.6, 132.1, 132.4, 133.3, 133.5, 135.3, 136.1, 137.4, 142.1, 187.3.