Acetone → (1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one

Participants

Reaction Steps

A solution of aq. NaOH solution (2 N, 125 mL) in EtOH (250 mL) was added to a mixture of benzaldehyde (26.5 g, 25 mmol) in acetone (9.2 mL, 13 mmol). The reaction mixture was stirred for 4 h at ambient temperature and the resulting yellow precipitate was filtered, washed with H2O, recrystallized from EtOAc and dried in vacuo to obtain NW275 as a yellow solid (23.1 g, 79%). mp: 106-107° C. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.78 (d, 3J=16.0 Hz, 2H, Hvin), 7.66-7.64 (m, 4H, HAr), 7.46-7.44 (m, 6H, HAr), 7.12 (d, 3J=16.0 Hz, 2H, Hvin). 13C NMR (75 MHz, CDCl3) δ (ppm): 189.3 (C), 143.7 (CH), 135.2 (C), 130.9 (CH), 129.4 (CH), 128.8 (CH), 125.8 (CH). MS (EI) m/z: 234.2 (M+). Anal. calcd for C17H14O: C, 87.15; H, 6.02. Found: C, 87.03; H, 6.03%.

Provenance & Evidence