Chloroacetic Acid → Oxydi(ethane-2,1-diyl) bis(chloroacetate)

Participants

Reaction Steps

In a 10-liter 4-neck round bottom flask equipped with a mechanical stirrer and Dean-Stark apparatus was added a solution of diethylene glycol (500 g), chloro acetic acid (980 g) and para-toluene sulphonic acid (25 g) in toluene (2.5 L). The solution was refluxed with stirring and azeotropic removal of water for 5 hours, and then cooled to room temperature. The toluene layer was washed with 5% sodium bicarbonate solution (3×1000 ml) and water (3 L). The toluene layer was dried over anhydrous sodium sulphate, filtered, and distilled to obtain chloro-acetic acid 2-[2-(2-chloro-acetoxy)-ethoxy]-ethyl ester (1.1 Kg) as light yellow oil. The product was characterized by 1H NMR (CDCl3) δ 3.75 (t, 2H, CH2), 4.12 (s, 2H, CH2), 4.36 (t, 2H, CH2)

Provenance & Evidence