Example 2 Synthesis of 2-(4-benzyloxyphenyl)ethanol
Methyl 2-(4-benzyloxyphenyl)acetate (7.8 mmol) was dissolved in anhydrous ether (5 mL) and added slowly and dropwise to a suspension of lithium aluminum hydride (15.8 mmol) in anhydrous ether (25 mL) at 0 °C. The reaction mixture was stirred overnight at room temperature and the reaction was subsequently quenched with water. The reaction mixture was extracted with ethyl acetate and the organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give 2-(4-phenylmethoxyphenyl)ethanol in quantitative yield.
1H-NMR (CDCl3): δ 7.28-7.47 (m, 5H); 7.17 (d, J = 8.7 Hz, 2H); 6.95 (d, J = 8.7 Hz, 2H); 5.07 (s, 2H); 3.85 (t, J = 6.6 Hz, 2H); 2.84 (t, J = 6.6 Hz, 2H).
[1] Patent: WO2007/139923, 2007, A1. Location in patent: Page/Page column 77
[2] Monatshefte fur Chemie, 1997, vol. 128, # 8-9, p. 863 - 879
[3] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 206, p. 103 - 116
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 4, p. 525 - 528
[5] Patent: US4672071, 1987, A
