Acetone → HCID 6172368, compound

Participants

Reaction Steps

A mixture of 4-formyl-benzonitrile (1.1 g, 8.4 mmol), acetone (308 μL, 4.2 mmol), LiClO4 (892 mg, 8.4 mmol) and Et3N (117 μL, 0.84 mmol) in toluene (8 mL) was stirred for 2 d at room temperature. A saturated aq. NH4Cl-solution was added to the reaction mixture and the resulting yellow suspension was extracted with CH2Cl2 and the combined organic layers were dried with MgSO4, filtered and evaporated in vacuo to afford NW307.2 as a yellow solid (300 mg, 25%). mp: 137-138° C. 1H NMR (250 MHz, DMSO-d6) δ (ppm): 8.00 (d, 3J=8.3 Hz, 4H, HAr), 7.87 (d, 3J=16.2 Hz, 2H, Hvin), 7.94 (d, 3J=8.4 Hz, 4H, HAr), 7.51 (d, 3J=16.1 Hz, 2H, Hvin). 13C NMR (75 MHz, DMSO-d6) δ (ppm): 188.5 (C), 141.2 (CH), 139.2 (C), 132.8 (CH), 129.2 (CH), 128.4 (CH), 118.6 (C), 112.4 (C). MS (FAB) m/z: 285.19 (M+). Anal. calcd for C19H12N2O: C, 80.27; H, 4.25; N, 9.85. Found: C, 80.04; H, 4.28; N, 9.76%.

Provenance & Evidence