108-55-4

100-51-6

54322-10-0

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).