Synthesis
The general procedure for the synthesis of 2-(2-chloroethoxy)acetic acid from 2-chloroethoxyethanol was as follows: ethylene glycol mono-2-chloroethyl ether (10 g, 0.08 mol) was mixed with a 30% aqueous hydrogen peroxide solution (22.8 g, 0.2 mol), followed by the addition of sodium sulfate dihydrate (0.53 g, 1.6 mmol) and tri-octylmethyl ammonium sulfate (0.75 g, 1.6 mmol). The reaction mixture was stirred at 90°C for 4 hours. Upon completion of the reaction, the reaction was quenched by the addition of aqueous sodium thiosulfate, and then the mixture was extracted with ethyl acetate (50 mL). The organic layers were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oily residue (9 g). The residue was diluted with ether and filtered to remove insoluble impurities. The filtrate was extracted by partitioning with the addition of aqueous sodium bicarbonate. The aqueous layer was washed with ether, acidified to pH 2-3 with dilute hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2-(2-chloroethoxy)acetic acid crude (2.14 g, 19.3% yield) as an oil.IR (neat): ν = 3410 (O-H), 1727 (C=O), 1123, 1044 cm1 .
References
[1] Tetrahedron Letters, 1996, vol. 37, # 28, p. 4837 - 4840
[2] Heterocycles, 2007, vol. 74, # C, p. 437 - 445
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 16, p. 3950 - 3955
[4] Patent: EP1640373, 2006, A1. Location in patent: Page/Page column 21
[5] Patent: WO2008/75152, 2008, A1. Location in patent: Page/Page column 40-41
