Chemical Properties
WHITE TO SLIGHTLY YELLOW CRYST. LOW MELTING MASS
Uses
It is used in the identification of sulfation sites of metabolites and prediction of the compounds? biological effects and in chemical investigation of Wedelia calendulacea.
Synthesis
General procedure for the synthesis of p-ethoxybenzyl alcohol from 4-ethoxybenzaldehyde: NaBH4 (0.8 g, 21.7 mmol) was added in batches to a stirring solution of 4-ethoxybenzaldehyde (3.0 g, 19.7 mmol) in methanol (50 mL) at 0 °C, and the addition process lasted for 15 minutes. After the addition, the reaction mixture was continued to be stirred at room temperature for 30 min. After completion of the reaction, the solvent was removed by rotary evaporator to obtain the crude product. The crude product was dissolved in water and extracted twice with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with water and saturated saline, and dried over anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to give a white solid product, p-ethoxybenzyl alcohol, in 82% yield. The product was analyzed by LC-MS showing [M+H]+ peak of 135.2. 1H-NMR (400 MHz, CDCl3) δ 7.266-7.286 (d, 2H, J = 8.0 Hz), 6.872-6.893 (d, 2H, J = 8.4 Hz), 4.609 (s, 2H), 4.010-4.061 (q, 2H, J = 6.8 Hz), 1.396-1.430 (t, 3H, J = 6.8 Hz).
References
[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 10, p. 1694 - 1698
[2] Patent: WO2010/127208, 2010, A1. Location in patent: Page/Page column 62
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4861 - 4868
[4] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
[5] Journal of the Chemical Society, 1956, p. 2455,246
