Acetone → 1,5-Bis(4-chlorophenyl)-1,4-pentadien- 3-one

Participants

Reaction Steps

A mixture of LiClO4 (1.2 g, 11 mmol), acetone (418 μL, 5.7 mmol) and 4-chloro-benzaldehyde (1.6 g, 11 mmol) was treated with TEA (159 μL, 1.1 mmol) and stirred for 4 min at ambient temperature. A saturated aq. NH4Cl solution was added to the reaction mixture and extracted with CH2Cl2. The combined organic layers were dried with MgSO4, filtered and the solvent was removed in vacuo. The residue was recrystallized from CH2Cl2 to obtain NW308 as yellow crystals (586 mg, 34%). mp: 182-184° C. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.60 (d, 3J=15.9 Hz, 2H, Hvin), 7.46 (d, 3J=8.5 Hz, 4H, HAr), 7.31 (d, 3J=8.5 Hz, 4H, HAr), 6.95 (d, 3J=15.9 Hz, 2H, Hvin). 13C NMR (75 MHz, CDCl3) δ (ppm): 188.3 (C), 142.0 (CH), 136.5 (C), 133.2 (C), 129.51 (CH), 129.2 (CH). MS (FAB) m/z: 303.1 (M+). Anal. calcd for C17H12Cl2O: C, 67.35; H, 3.99; Cl, 23.39. Found: C, 67.33; H, 4.01; Cl, 23.17%.

Provenance & Evidence