2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER Chemical Properties

Boiling point:

130 °C / 9mmHg

Density 

1.23

refractive index 

1.4480

Flash point:

108℃

storage temp. 

0-10°C

pka

5.24±0.46(Predicted)

form 

clear liquid

color 

White to Yellow to Green

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2918300090

2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER Usage And Synthesis

Synthesis

NaOtBu (96.1 g, 1.0 mol) was dissolved in THF (1 L) and the solution was cooled to 0°C. A mixture of ethyl chloroacetate (107 mL, 1.0 mol) and diethyl oxalate (136 mL, 1.0 mol) was added slowly and dropwise at this temperature under vigorous mechanical stirring. After the reaction mixture was stirred overnight at room temperature, an aqueous HCl solution (90 mL of concentrated hydrochloric acid mixed with 400 mL of water) was added. The resulting solution was extracted with CH2Cl2 (3 x 200 mL). The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reduced pressure distillation (boiling point range 110-140°C, pressure 10 torr). The product diethyl 2-chloro-3-oxosuccinate was obtained 157.6 g in 71% yield.1H NMR (CDCl3, 400 MHz) δ= 1.31 (t, J = 7.2Hz, 3H), 1.39 (t, J = 7.2Hz, 3H), 4.31 (q, J = 7.2Hz, 2H), 4.39 (q, J = 7.2Hz, 2H), 4.39 (q, J = 7.2Hz, 2H) 5.46 (s, 1H).

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 367 - 391
[2] Patent: CN104177296, 2017, B. Location in patent: Paragraph 0043; 0044; 0045
[3] Macromolecules, 2011, vol. 44, # 23, p. 9146 - 9154
[4] Chemische Berichte, 1910, vol. 43, p. 3529
[5] Bulletin des Societes Chimiques Belges, 1975, vol. 84, p. 341 - 360

2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER(34034-87-2)Related Product Information

• Oxaloacetic acid
• Dichloromethane
• Ethyl 2-chloropropionate
• ETHYL 4-METHOXY-3-OXO-BUTANOATE
• Methyl 2-chloroacetoacetate
• CHLOROSUCCINIC ACID
• 2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER
• Ethyl 2-chloroacetoacetate
• Methyl 4-methoxyacetoacetate
• Ethyl 3-chloropropionate
• 2-Chloro-3-oxopropionic acid ethyl ester
• 3-CHLOROPYRUVIC ACID
• dimethyl chlorooxosuccinate