Iodoacetic Acid → 2-(2-Ethoxyethoxy)acetic acid

2-Ethoxyethanol (0.88 mL, 11 mmol) and sodium hydride (60% in oil, 1.08 g, 27 mmol) were stirred in DMF (20 mL) for 5 min. Iodoacetic acid (2.02 g, 10.9 mmol) was dissolved in DMF (20 mL) and added dropwise to the suspension. The thick orange suspension was stirred at rt for 3 hours. The reaction was quenched by slowly adding water (10 mL), followed by hydrochloric acid (4 M, 5 mL). The reaction mixture was extracted with dichloromethane (3×50 mL) and the combined organic layers dried over sodium sulfate, filtered and evaporated yielding a clear oil. The residue was purified by distillation under reduced pressure to give the product (1.1 g, 68%) as an oil.