Reaction Steps
Into a 5 mL round-bottom flask was introduced selenium dioxide (71 mg, 0.64 mmol), 1 mL of dichloromethane, and 90% t-butyl hydroperoxide (0.284 mL, 2.56 mmol). After the mixture had been stirred for 30 min. at room temperature, 2-(5,5,8,8-tetramethyl-3-propyloxy-5,6,7,8-tetrahydronaphthalen-2-yl)-propene (366 mg, 1.28 mmol), in 1 mL of dichloromethane was slowly added. The mixture was stirred at room temperature for 3 h. Then quenched with aqueous saturated NaHCO3. The mixture was extracted with dichloromethane (2×10 mL), washed with water (10 mL) and brine (10 mL), and the combined organic phase dried (Na2SO4). Concentrated in vacuo to give an oil which was subjected to chromatography (10% EtOAC/90% hexane) to give 149 mg (40%) of 2-(5,5,8,8-tetramethyl-3-propyloxy-5,6,7,8-tetrahydro naphthalen-2-yl)-propen-1-ol. 1H NMR (400 MHz, (CDCl3) δ 7.14(s, 1H, aromatic), 6.76(s, 1H, aromatic), 5.36(s, 1H, vinylic), 5.22(s, 1H, vinylic), 4.44(d, J=6.1 Hz, CH2OH), 3.93(t, J=6.5 Hz, 2H, CH2), 2.19(t, J=6.1 Hz, 1H, OH), 1.82(sx, J=6.8 Hz, 2H, CH2), 1.66(s, 4H, 2CH2), 1.28(s, 6H, 2CH3), 1.26(s, 3H, CH3), 1.25(s, 3H, CH3) and 1.03(t, J=7.3 Hz, 3H, CH3).
