Sodium Acetate → HCID 14692980, compound

Participants

Reaction Steps

A solution of α,2,2,4,6,6-hexamethyl-γ-methylene-3-cyclohexene-1-propanol (2.36 g, 0.01 mol) in dichloromethane (10 mL) was added over a 30 min period to a mixture of pyridinium chlorochromate (3.25 g, 0.015 mol), sodium acetate (2.30 g, 0.03 mol) and dichloromethane (15 mL) at 25° C. The mixture was filtered and the filtrate washed with water (100 mL) and 5% sodium carbonate solution (100 mL). The solvents were evaporated and the residue chromatographed to provide after kugelrohr distillation 1.75 g (75% yield) of 4-(2,2,4,6,6-pentamethyl-3-cyclohexen-1-yl)-4-penten-2-one (GLC purity: 94%). 1H-NMR δ0.93 (3H, s) 0.95 (3H, s), 1.02 (6H, s), 1.62 (3H, s), 1.6-1.8 (2H, m), 1.97 (1H, s), 2.18 (3H, s), 3.15 (2H, s), 5.05 (2H, broad s); IR (film) vmax 2950, 1710, 1630, 1430, 1380, 1350 cm-1 ; MS m/e 234, 219, 201, 191, 176, 161, 149, 123, 96.

Provenance & Evidence