Ammonia → HCID 14692992, compound

Participants

Reaction Steps

Lithium shot (0.5 g, 0.071 mol) was added portionwise over a 40 min. period to a cold (-30° to -40° C.) mixture of 4-(2,2,4,6,6-pentamethyl-3-cyclohexen-1-yl)-3-penten-2-one (1.08 g, 0.0046 mol), ether (20 mL), ethanol (20 mL) and ammonia (80 mL). Ammonium chloride (8.0 g) was added to the blue colored reaction mixture. The ammonia was allowed to evaporate. Ether (100 mL) and water (200 mL) were added to the residue. The aqueous layer was extracted with ether (100 mL). The combined organic extracts were washed with 0.5N HCl (2×100 mL), saturated sodium bicarbonate solution (100 mL) and dried. Evaporation of solvents, chromatography of the residue and kugelrohr distillation provided 0.850 g (78% yield) of α,γ,2,2,4,6,6-heptamethyl-3-cyclohexene-1-propanol. GLC analysis shows 4 isomers of 4.1%, 12.8% and 82.3% (two peaks incompletely resolved). 1H-NMR (60 MHz, CDCl3) δ0.98 and 1.05 (12H, 2s), 1.12 (3H, d, J=6 Hz), 1.25 (3H, d, J=4 Hz), 1.60 (3H, s), 1.0-2.5 (7H, m), 3.6-4.1 (1H, m), 5.00 (1H, broad s). IR (film) vmax 3320, 2950, 1640, 1470, 1450, 1380, 1360 cm-1 ; Ms m/e 238, 223, 180, 151, 109, 96.

Provenance & Evidence