ChemicalBook CAS DataBase List MONO-METHYL SUCCINATE

MONO-METHYL SUCCINATE synthesis

13synthesis methods

Product Name:MONO-METHYL SUCCINATE
CAS Number:3878-55-5
Molecular formula:C5H8O4
Molecular Weight:132.11

108-30-5 Synthesis

108-30-5
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3878-55-5
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Yield:3878-55-5 93.6% (98.886 g)

Reaction Conditions:

in methanol

Steps:

3 mono-methyl succinate (20)
mono-methyl succinate (20) A mixture of succinic anhydride (80.02 g; 799.6 mmole) and dry methanol (38.9 mL; 30.77 g; 960.4 mmole) was shaken vigorously while heated at reflux with a steam bath until all the succinic anhydride had been dissolved (a period of about 18 minutes). The flask was then immerse in the steam bath and the mixture was heated at reflux for an additional 25 minutes. The excess of methanol was removed under reduced pressure and the residue was cooled with an ice bath. The white precipitate was filtered off and triturated with water. The solid was dried under vacuum until constant weight. Thus, mono-methyl succinate (20) was recovered in an excellent yield of 93.6% (98.886 g). ¹H NMR (in CDCl₃; 400 MHz): 3.71 (s, 3H, C₃O₂CCH₂CH₂CO₂H), 2.71 (dd, 1H, J=2.1 and 5.8 Hz, CH₃O₂CC_αCH₂CO₂H), 2.69 (dd, 1H, J=1.2 and 5.7 Hz, CH₃O₂C-C_βCH₂CO₂H), 2.65 (dd, 1H, J=1.1 and 5.6 Hz, CH₃O₂CCH₂C_αCO₂H), and 2.63 ppm (dd, 1H, J=2.1 and 5.8 Hz, CH₃O₂CCH₂C_βCO₂H). ¹³C NMR (in CDCl₃; 100 MHz): 178.75 (1C, CH₃O₂CCH₂CH₂O₂H), 173.04 (1C, CH₃O₂CH₂CH₂CO₂H), 52.40 (1C, H₃O₂CCH₂CH₂CO₂H), 29.33 (1C, CH₃O₂CCH₂H₂CO₂H), and 29.02 ppm (CH₃O₂C-H₂CH₂CO₂H). Melting Point: 55.5 to 57° C.