Methyl iodide → HCID 14692991, compound

Participants

Reaction Steps

Sodium hydride (0.6g of 60% oil dispersion, 0.015 mol) was washed with hexane (2×3 mL) and suspended in THF (10 mL). A solution of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol (1.11g, 0.005 mol) in THF (5 mL) was added, followed by methyl iodide (1.4g, 0.001 mol). The mixture was heated at reflux for 4 hr. Afterwhich, work-up, chromatography and kugelrohr distillation gave 1.10g of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol methyl ether. 1H-NMR (60 MHz, CDCl3) δ0.95 (6H, s), 1.03 (6H, broad s), 1.63 (3H, broad s), 1.5-2.6 (5H, m), 3.33 (3H, s) 3.58 (2H, t, J =7 Hz), 4.85-5.15 (3H, m); IR (film) vmax 2960, 1640, 1440, 1380, 1360 cm-1 ; MS m/e 236, 221, 204, 189, 140, 125, 96.

Provenance & Evidence