Synthesis
General procedure for the synthesis of methoxyethoxyacetic acid from 2-methoxyethanol and tert-butyl bromoacetate: 2-methoxyethanol (10 g, 131.4 mmol) and potassium tert-butoxide (17.67 g, 157.68 mmol) were dissolved in 100 mL of tetrahydrofuran (THF). The reaction mixture was heated to 45 °C, maintained for 1 h and then cooled to room temperature. To the above mixture was added tert-butyl bromoacetate (25.63 g, 131.41 mmol) and the reaction was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was concentrated and the residue was dissolved in water. The pH of the aqueous phase was adjusted to 12-12.5 with 1 M sodium hydroxide aqueous solution and stirring was continued for 12-14 hours at room temperature. Subsequently, the pH of the aqueous phase was adjusted with 10% aqueous phosphoric acid solution to 2. The product was extracted with dichloromethane (DCM). The DCM was removed by rotary evaporator to give 2-(2-methoxyethoxy)acetic acid as an oil (4.1 g, 23% yield).
