Reaction Steps
3,4-Didecyloxybenzaldehyde (6.78 g., 16.2 mmol, 1 equiv.) is dissolved in 44 mL of methanol and 20 mL of THF. Sodium borohydride (0.613 g., 16.2 mmol, 1 equiv.) is added in portions. The mixture is stirred for 30 minutes at room temperature. The solution is poured into saturated ammonium chloride solution, and then extracted twice with EtOAc. The organic extracts are washed with brine, dried (MgSO4), and evaporated. Chromatography on silica gel using 10%-20% EtOAc/hexane affords 3,4-didecyloxybenzyl alcohol (12a) (5.71 g., 13.6 mmol, 84%) as a clear oil: mp=41°-42.5° C.; UVmax (EtOH) 206 nm (ε=19085), 232 nm (ε=5340), 280 nm (ε=2239); 1H NMR (300 MHz, CDCl3) δ 6.90 (s, 1H, ArH), 6.83 (s, 1H, ArH), 6.83 (s, 1H, ArH), 4.58 (d, J=6 Hz, 2H, ArCH2OH), 3.96 (m, 4H, RCH2O), 1.79 (m, 4H, RCH2CH2O), 1.58 (t, J=6 Hz, 1H, OH), 1.44 (m, 4H, decyl), 1.25 (m, 24H, decyl), 0.86 (m, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 149.34, 148.72, 133.68, 119.58, 113.83, 112.95, 69.42, 69.21, 65.41, 31.92, 29.64, 29.59, 29.43, 29.36, 29.30, 26.04, 22.69, 14.12; IR (KBr) 3346, 2956, 2922, 2850, 1520, 1468, 1262, 1236, 1138 m-1 ; MS (DCI) m/e 421 (MH+), 403 (M--OH). Anal. Calcd for C27H48O3 : C, 77.09; H, 11.50. Found: C, 77.26; H, 11.61.
