2-[(benzyloxy)methyl]propane-1,3-diol

Synthesis

5-((Benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane (5.54 g, 23.44 mmol) was used as a starting material, which was dissolved in methanol (20 mL), followed by the slow addition of 3 N hydrochloric acid (3 mL). The reaction mixture was stirred at 25 °C for 30 min. Upon completion of the reaction, the pH was adjusted to 8 with solid sodium bicarbonate, followed by solvent evaporation. The residue was dissolved in ethyl acetate, filtered through a short silica gel pad and washed with ethyl acetate. The filtrate was concentrated in vacuum to afford 2-((benzyloxy)methyl)propane-1,3-diol (4.39 g, 95% yield) as an off-white solid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 1.99-2.07 (m, 1H, CH), 2.74 (s, 2H, 2×OH), 3.60 (d, J = 5.7 Hz, 2H, OCH2), 3.78 (d, J = 5.4 Hz, 4H, 2×OCH2), 4.50 (s, 2H, OCH2Ar). 7.25-7.38 (m, 5H, Ar).

References

[1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 239 - 250
[2] Patent: US2008/21032, 2008, A1. Location in patent: Page/Page column 81
[3] Patent: WO2018/149419, 2018, A1. Location in patent: Paragraph 001322; 001323
[4] Patent: WO2016/145142, 2016, A1. Location in patent: Page/Page column 352
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 20, p. 2909 - 2914