Sodium Methoxide → HCID 56998058, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2,2,4,6,6,-pentamethyl-3-cyclohexen-1-yl)-4-penten-2-one (1.50 g, 0.0063 mol) methanol (30 mL) and sodium methoxide (0.02 g) was stirred at 25° C. for 18 hr. The mixture was then heated at reflux for 3 hr. The mixture was cooled to 25° C. and most of the methanol was evaporated under reduced pressure. The residue was partitioned between ether (75 mL) and water (15 mL). The aqueous layer was extracted with ether (50 mL). The ether extracts were washed with saturated sodium bicarbonate solution, brine and dried. Evaporation of solvents and kugelrohr distillation of the residue provided 1.28 g (85% yield) of 4-(2,2,4,6,6-pentamethyl-3-cyclohexen-1-yl)-3-penten-2-one (GLC purity: 93.5%). 1H-NMR (60 MHz) δ0.93 (12h, broad s), 1.57 (3H, broad s), 1.5-1.9 (2H, m), 1.88 (1H, broad s), 3.42 (3H, s), 5.01 (1H, broad s), 6.02 (1H, broad s); IR (film) vmax 2950, 1685, 1600, 1440, 1380, 1365 cm-1 ; MS m/e 234, 216, 191, 149, 135, 121.

Provenance & Evidence