Acetic Anhydride → HCID 14692990, compound

Participants

Reaction Steps

A solution of acetic anhydride (0.23 mL) in dichloromethane (2 mL) was reacted with a mixture of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol (0.56 g, 0.0025 mol), triethylamine (0.41 mL), 4-dimethylaminopyridine (0.031 g) and dichloromethane at 25° C. Work-up, chromatography and distillation gave 0.60 g of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol acetate bp (kugelrohr bath 110°-120° C.), 0.5 mm (GLC purity: 88%). 1H-NMR (60 MHz, CDCl3) δ0.93 (6H, s), 1.00 and 1.02 (6H, 2s), 1.60 (3H, s), 2.00 (3H, s), 0.9-2.6 (5H, m), 4.20 (1H, t, J=7 Hz), 4.86-5.07 (3H, m); IR (film) vmax 2960, 1735, 1635, 1440, 1370, 1350 cm-1 ; MS (m/e) 264, 249, 221, 204, 189, 108, 96.

Provenance & Evidence