Propanal → HCID 14692984, compound

Participants

Reaction Conditions

Reaction Steps

Dimethylaluminum chloride (60 mL of a 1 M hexane solution) was added dropwise to a solution of 1,3,3,5,5-pentamethyl-4-(1-methylethenyl)-1-cyclohexene (7.70g, 0.04 mol) and propionaldehyde (2.30g, 0.04 mol) in dichloromethane (150 mL) at 25°-30° C. over a 15 min period. The mixture was stirred at 25° C. for 16h. Work-up (as described in Example 2) and chromatography provided 2.20g of α-ethyl-2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol, bp (kugelrohr bath) 125° C., 0.5 mm, (GLC purity, two isomers, 40.7% and 57.9%). 1H-NMR (60 MHz, CDCl3) δ0.98 and 1.03 (12H, 2s), 1.02 (3H, t, J =4 Hz), 1.63 (3H, s), 1.1-2.6 (8H, m), 3.5-3.9 (1 H, m), 5.0-5.3 (3H, broad s); IR (film) vmax 3350, 2950, 1640, 1460, 1380, 1360 cm-1 ; MS m/e 250, 235, 217, 125, 107, 96. The mass spectra of the diastereomers were nearly identical.

Provenance & Evidence