103-40-2

108-30-5

121-44-8

103-40-2

At 0 °C, 4.13 mL (4.32 g, 40 mmol) of benzyl alcohol and 4.40 g (44 mmol) of succinic anhydride were dissolved in 100 mL of tetrahydrofuran (THF). Subsequently, 12.24 mL (8.90 g, 88 mmol) of triethylamine was added rapidly. The reaction mixture was gradually warmed to room temperature and stirred continuously for 18 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure to give a viscous oil. The oily substance was dissolved in a mixture of 100 mL of 1N hydrochloric acid and 100 mL of ethyl acetate (EtOAc) for liquid-liquid partitioning. The ethyl acetate layer was extracted with 84 mL of 5% sodium bicarbonate (NaHCO3) solution. The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and subsequently extracted with two 50 mL portions of ethyl acetate. All ethyl acetate layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated to afford 6.9 g (83% yield) of the target product monobenzyl butanedioate (21) as a white bulk solid. Its 1H NMR (CDCl3) data were as follows: δ 2.70 (s, 4H), 5.22 (s, 2H), 7.38 (s, 5H).