A benzene solution of 1 eq of diethylaluminum chloride was added dropwise at 0° to a solution of 1 eq of lithium 2,2,6,6-tetramethylpiperidide prepared in the usual fashion in benzene. The resulting slurry was stirred for 30 minutes and used immediately.
To a stirred mixture of 0.004 mol of diethylaluminum 2,2,6,6-tetramethylpiperidide in 10 mL of benzene at 0 °C was added dropwise over 5 minutes a solution of 0.18 g (0.001 mol) of epoxide in 3 mL of benzene. The mixture was stirred at 0 °C until analysis indicated the absence of starting material. The reaction was quenched by the addition of ice-cold 1 N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with ether. The organic layers were combined, washed with brine, dried, and concentrated. The residue was purified by preparative TLC (R 0.22 in 1:2 ether–hexane) to give 99% of (E)-2-cyclododecenol: IR (neat) 3330–3370, 1465, 1450, 970 cm; NMR (CCl) δ 3.73–4.20 (1, m), 4.97–5.82 (2, m); mass spectrum (m/z) 182 (16), 164 (13), 139 (32), 125 (46), and 98 (100).