Water → Propanoic acid, 2-chloro-, oxydi-2,1-ethanediyl ester

Participants

Reaction Steps

In a 20 L glass reactor equipped with a Dean-Stark apparatus was added a solution of diethylene glycol (1500 g), 2-chloropropionic acid (3200 g) and para-toluene sulphonic acid (50 g) in toluene (5 L). The reaction mixture was refluxed for 5 hours with azeotropic removal of water, and then cooled to room temperature. The toluene layer was washed with 5% sodium bicarbonate solution (4500 ml) and water (4 L). The toluene layer was dried over anhydrous anhydrous sodium sulphate, and distilled to obtain 2-chloropropionic acid 2-[2-(2-chloropropionyloxy)-ethoxy]-ethyl ester (3.3 Kg) as light yellow oil. The product was characterized by 1H NMR (CDCl3) δ 1.65 (d, 3H, CH3), 3.75 (t, 2H, CH2), 4.40 (t, 2H, CH2), 4.48 (q, 1H, CH)

Provenance & Evidence