Benzene → HCID 118366098, compound

Participants

Reaction Steps

10.79 g (0.11 mol) of cyclohexanone and 10.4 g (0.12 mol) of morpholine were added to 20 mL benzene, refluxed azeotropically after a trap was equipped, when no water was generated, benzene and morpholine were evaporated under reduced pressure to give enamine. 6.54 g (0.043 mol) of enamine and 5.40 g (0.033 mol) of 3,5-dimethoxybenzaldehyde were added to 20 mL benzene, refluxed azeotropically after a trap was equipped until no water was generated in a total of 8 h, after cooling to room temperature, 6 mol/L hydrochloric acid was added slowly with stirring, and stirred at room temperature for 2 h, the benzene layer was separated, the aqueous layer was extracted with benzene layer, benzene layers were combined and dried over anhydrous sodium sulfate, after evaporating the solvent under reduced pressure and recrystallizing with petroleum ether and ethanol, E-2-(3,5-dioxobenzylidene)cyclohexanone was obtained as yellow needles, yield: 74%, mp 55.0˜56.6. 1H-NMR: δ: 7.41 (s, 1H, ═CH), 6.53 (d, 2H, J=2.0 Hz, ArH), 6.45 (t, 1H, J=2.0 Hz, ArH), 3.80 (s, 6H, OCH3), 2.84 (dt, 2H, J=1.9, 6.5 Hz, CH2), 2.54 (t, 2H, J=6.6 Hz, CH2), 1.90 (m, 2H, CH2), 1.78 (m, 2H, CH2).

Provenance & Evidence