Acetone → HCID 5463280, compound

Participants

Reaction Steps

A solution of NaOH (1.4 g, 142 mmol) in H2O (60 mL) and EtOH (60 mL) was added to a mixture of 2-chlorobenzaldehyde (8 mL, 72 mmol) in acetone (2.6 mL, 36 mmol). The reaction mixture was stirred for 1d at room temperature and the resulting precipitate was filtered, washed with H2O, recrystallized from EtOAc and dried in vacuo to obtain NW268 as a bright yellow solid (7.4 g, 69%). mp: 107-109° C. 1H NMR (250 MHz, CDCl3) δ (ppm): 8.15 (d, 3J=16.0 Hz, 2H, Hvin), 7.79-7.66 (m, 2H, HAr), 7.51-7.29 (m, 6H, HAr), 7.08 (d, 3J=16.0 Hz, 2H, Hvin). 13C NMR (75 MHz, CDCl3) δ (ppm): 188.7 (C), 139.3 (CH), 135.4 (C), 133.0 (C), 131.2 (CH), 130.2 (CH), 127.7 (CH), 127.5 (CH), 127.1 (CH). MS (FAB) m/z: 303.1 (M+). Anal. calcd for C17H12Cl2O: C, 67.35; H, 3.99; Cl, 23.39. Found: C, 67.09; H, 4.06; Cl, 22.65%.

Provenance & Evidence