Reaction Steps
(Not Shown) A solution of ethyl 2,6,6-trimethyl-2,4-cyclohexadiene-1-carboxylate III (9.09 g, 0.0468 mol) in anhydrous diethyl ether (100 mL) was slowly added to a suspension of LiAlH4 (3.75 g, 0.099 mol) in diethyl ether (200 mL) at 0° C. The mixture was stirred for 4 h and monitored by thin layer chromatography (TLC). Water (4.0 mL) was carefully added, followed by 15% NaOH (4.0 mL) and water (12 mL). The white precipitate was filtered and rinsed with warm EtOAc (100 mL). EtOAc (100 mL) was added and the combined organic layer was washed with water (3×50 mL), brine (3×50 mL), dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (hexanes:EtOAc 4:1) to give 6.15 g (87% yield) of pure 2,6,6-trimethyl-2,4-cyclohexadiene-1-methanol; IR (neat) 3340 (--OH), 2958 (CH aliph.), 1467 (C=C), 1442, 1375, 1357, 1049, 1012 cm-1 ;1H-NMR (CDCl3 ; 400 MHz) δ (ppm): 5.76 (m, 1 H, H3), 5.69 (m, 1 H, H2), 5.36 (d, 9.4 Hz, 1 H, H4), 3.73 (m, 2 H, --CH2OH), 1.85 (s, 3 H, --CH3, ring), 1.77 (t, J=4.1 Hz, 1 H, OH), 1.55 (t, J=5.0 Hz, 1 H, CH ring), 1.14 (s, 3 H, gem CH3), 1.02 (s, 3 H, gem CH3); 13C-NMR (CDCl3 ; 100 MHz) δ (ppm): 2 diastereomers: 136.6, 135.2, 135.0, 122.3, 120.7, 120.3, 118.8, 63.1, 61.7, 61.6, 60.3, 52.2, 50.9, 33.7, 28.1, 26.9, 25.4, 24.1, 22.5, 21.2.
