209542-49-4

111-77-3

1663-39-4

209542-49-4

The general procedure for the synthesis of 3-(2-(2-methoxyethoxy)ethoxy)propionic acid from diethylene glycol monomethyl ether and tert-butyl acrylate is as follows: 1. 110 mL (0.93 mol) of 2-(2-methoxyethoxy)ethanol and 50 mL of dehydrated THF were added to a 500 mL four-neck flask under argon protection. 2. After cooling the reaction system to 0 °C, 1.4 g (0.06 mol) of sodium metal was slowly added. 3. After confirming that no gas was produced in the reaction solution, a solution of 44 mL (0.31 mol) of tert-butyl acrylate (dissolved in 50 mL of THF) was slowly added dropwise. 4. After the dropwise addition was completed, the reaction system was slowly warmed from 0°C to room temperature and stirred at room temperature for 24 hours. 5. Upon completion of the reaction, THF was removed by distillation under reduced pressure. 6. 100 mL (0.3 mol) of 3 mol/L aqueous sodium hydroxide was added to the residue and stirred for 5 hours. 7. The pH of the reaction solution was adjusted to 2 with 10% aqueous sulfuric acid and then extracted three times with dichloromethane. 8. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. 9. The crude product was distilled twice under reduced pressure at 140 °C and 0.1 kPa to obtain 14 g of 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid (yield: 24%). The 1H-NMR data of the product 3-[2-(2-methoxyethoxy)ethoxy]propionic acid are as follows: 1H-NMR (DMSO-d6) δ (ppm): 2.67 (q, 2H), 2.51 (q, 2H), 2.07 (s, 3H).