Mono-methyl succinate synthesis
- Product Name:Mono-methyl succinate
- CAS Number:3878-55-5
- Molecular formula:C5H8O4
- Molecular Weight:132.11
108-30-5
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3878-55-5
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$9.00/1g
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, CH3O2CCαCH2CO2H), 2.69 (dd, 1H, J=1.2 and 5.7 Hz, CH3O2C-CβCH2CO2H), 2.65 (dd, 1H, J=1.1 and 5.6 Hz, CH3O2CCH2CαCO2H), and 2.63 ppm (dd, 1H, J=2.1 and 5.8 Hz, CH3O2CCH2CβCO2H). 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.
References:
Flanagan, Richard J.;Dufour, Jean-Marc US2002/76377, 2002, A1
67-56-1
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110-15-6
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3878-55-5
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106-65-0
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106-65-0
464 suppliers
$6.00/25g
3878-55-5
244 suppliers
$9.00/1g