Synthesis
1-Bromo-4-decylbenzene was synthesized by the Wolff-Kishner reaction using 1-(4-bromophenyl)decan-1-one 7 (1.3 g, 4.2 mmol) as raw material. The procedure was as follows: 1-(4-bromophenyl)decan-1-one 7, hydrazine monohydrate (1.2 mL, 16 mmol) and KOH (1.8 g, 32 mmol) were dissolved in 25 mL of 1-octanol in a 50 mL two-neck flask to form a green suspension. The reaction mixture was stirred at reflux for 2 h at 135 °C until the solution was almost colorless. After completion of the reaction, the mixture was cooled to room temperature, diluted with ether (50 mL) and washed sequentially with aqueous 1N HCl (50 mL), aqueous 2N HCl (20 mL) and brine (2 x 30 mL). The organic phase was dried over MgSO4, filtered and concentrated in vacuum. 1-Octanol was removed by vacuum distillation to give about 2.7 g of crude product. The crude product was purified by column chromatography using heptane as eluent to give a final colorless oily product in 40% yield. The product was detected by TLC (Rf = 0.61, 100% heptane).1H NMR (500 MHz, CDCl3) δ 7.37 (d, J = 8.3Hz, 2H), 7.03 (d, J = 8.1Hz, 2H), 2.54 (t, J = 7.7Hz, 2H), 1.60-1.54 (m, 2H), 1.28-1.25 (m, 2H). 14H), 0.88 (t, J = 6.8 Hz, 3H).13C NMR (50 MHz, CDCl3) δ 142.05, 131.46, 130.37, 119.47, 35.59, 32.14, 31.56, 29.85, 29.82, 29.71, 29.57, 29.43, 22.93. 14.34. ms (APPI): m/z 296.2 [M+].
References
[1] Macromolecules, 2010, vol. 43, # 19, p. 8063 - 8070
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 2, p. 541 - 548
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7763 - 7778
[4] Journal of Materials Chemistry, 2003, vol. 13, # 1, p. 50 - 55
[5] Molecular Crystals and Liquid Crystals, 2003, vol. 396, p. 241 - 250
