Synthesis
Sodium borohydride (5.06 g, 133 mmol) was added in portions to a solution of 2-(carboxymethyl)-4-nitrobenzoic acid (10.0 g, 44.4 mmol) in THF (220 mL). The contents were cooled to 0 °C, and boron triflfluoride diethyl etherate (21.3 mL, 133 mmol) was added dropwise over 1 h. The mixture was allowed to warm to 25 °C and stirred for 16 h. The reaction mixture was then cooled to 0 °C and cautiously quenched with aqueous sodium hydroxide (1 N, 178 mL). The contents were stirred for 3 h, and the THF was removed under vacuum. The resulting aqueous suspension was cooled to 0 °C and the product was fifiltered off. After drying, 7.78 g (89%) of the diol was afforded as a white solid.
