Synthesis of 1- (benzyloxy)-4-((benzyloxy)methyl)benzene (30)

To a solution of alcohol 29 (3 mmol) in anhydrous THF (30ml) was added sodium hydride (60% dispersion in mineral oil, 6 mmol) at 0°C. The suspension was stirred at 0°C for 30 minutes. Benzyl bromide (4 mmol) was added to the suspension. The mixture was stirred at r.t for 3 hours. Water was added to the suspension, the mixture became homogeneous. The mixture was extracted by ethyl acetate and washed with brine, dried over anhydrous sodium sulfate and concentrated to get the crude. The crude compound was purified by flash chromatography (ethyl acetate: hexane 1:3). ¹H NMR (400 MHz, Chloroform-d) δ 7.52 – 7.18 (m, 12H), 7.03 – 6.83 (m, 2H), 5.07 (s, 2H), 4.53 (s, 2H), 4.49 (s, 2H).