Synthesis
GENERAL METHOD: To a solution of glutaric anhydride (1.0 g, 10 mmol) in DMF (4 mL) was slowly added benzyl alcohol (0.94 mL, 9.09 mmol) and N,N-diisopropylethylamine (DIEA, 1.93 mL, 11 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed using a rotary evaporator (Speed-vac). The residue was dissolved in ethyl acetate (50 mL) and washed sequentially with saturated sodium chloride solution (10 mL x 2). The organic phase was separated and extracted with aqueous sodium bicarbonate solution (5M, 5mL x 3). The aqueous phase extracts were combined and the pH was adjusted to 4 with aqueous citric acid (5M) and extracted with ethyl acetate (30mL × 3). All ethyl acetate extracts were combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 1,5-glutaric acid monobenzoate as a white solid (1.66 g, 89% yield).
References
[1] Chemical Biology and Drug Design, 2018, vol. 92, # 2, p. 1403 - 1408
[2] Synthetic Communications, 2001, vol. 31, # 9, p. 1399 - 1419
[3] Journal of the American Chemical Society, 1996, vol. 118, # 29, p. 6826 - 6840
[4] Chemical Communications, 2011, vol. 47, # 17, p. 4896 - 4898
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7507 - 7514
