2-Cyclohexen-1-one → HCID 54269430, compound

Participants

Reaction Steps

N-(3-Phenylpropylidene)methylamine N-oxide (1.50 g, 9.19 mmol) and 2-cyclohexenone (5 ml) were heated at 80°-90° C. for 24 hours in a sealed tube under nitrogen. The solution was cooled to room temperature and the excess 2-cyclohexenone was removed under reduced pressure using Kugelrohr distillation to yield the crude product as a dark yellow oil (2.36 g, 99%). The crude product was purified by flash chromatography using 60:40 v/v light petroleum (fraction of bp 40°-60° C.):ethyl acetate as the solvent system to give the title compound as a colourless oil (2.11 g, 89%), vmax (film) 2941, 2872, 1710, 1454, 1235 cm-1 ; δH (250 MHz, CDCl3 --Me4Si) 1.70-2.0 (6H, br m), 2.25-2.55 (2H, m), 2.60-2.80 (2H, m), 2.70 (3H, s), 2.75 (1H, t), 3.25 (1H, br m), 4.45 (1H, br m), 7.10-7.30 (5H, br m); M/z 259 (M+ 100%) (Found: M+ 259.1572; C16H21NO2 requires M+ 259.1603).

Provenance & Evidence