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ChemicalBook--->CAS DataBase List--->487-66-1

487-66-1

487-66-1 Structure

487-66-1 Structure
IdentificationBack Directory
[Name]

2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid
[CAS]

487-66-1
[Synonyms]

2-propionic-3-methylmaleic anhydride
2-(2-Carboxyethyl)-3-methylmaleic Anhydride
2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid
2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoicAcid>
3-Furanpropanoic acid, 2,5-dihydro-4-methyl-2,5-dioxo-
3-(4-Methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoic acid
3-(4-methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoic acid (Related Reference)
[Molecular Formula]

C8H8O5
[MDL Number]

MFCD18252872
[MOL File]

487-66-1.mol
[Molecular Weight]

184.146
Chemical PropertiesBack Directory
[Melting point ]

97.0 to 101.0 °C
[Boiling point ]

391.0±25.0 °C(Predicted)
[density ]

1.408±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[form ]

powder to crystal
[pka]

4.31±0.10(Predicted)
[color ]

White to Almost white
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P305+P351+P338
[HS Code ]

2932.19.5100
Spectrum DetailBack Directory
[Spectrum Detail]

2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid(487-66-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

Dimethyl 2-oxoglutarate

13192-04-6

TRIETHYL 2-PHOSPHONOPROPIONATE

3699-66-9

2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid

487-66-1

Example 4: Synthesis of Masking Agent A - Preparation of 2-propanoic acid-3-methylmaleic anhydride (carboxydimethylmaleic anhydride or CDM) precursor 1. Suspend sodium hydride (0.58 g, 25 mmol) in 50 mL of anhydrous tetrahydrofuran to which triethyl 2-phosphonopropyl ester (7.1 g, 30 mmol) was added. After the hydrogen release stopped, dimethyl α-ketoglutarate (15 g, 20 mmol) dissolved in 10 mL of anhydrous tetrahydrofuran was added and the reaction mixture was stirred for 30 minutes. 2. Upon completion of the reaction, 10 mL of water was added and the tetrahydrofuran was removed by rotary evaporation. The resulting solid-water mixture was extracted with ether (3 x 50 mL). The ether layers were combined, dried with magnesium sulfate and concentrated to give a light yellow oil. 3. The above oil was purified by silica gel column chromatography with the eluent of ether:hexane (2:1) to give 4 g of pure triglyceride (82% yield). 4. The resulting triglyceride was dissolved in 50 mL of a solvent mixture of water and ethanol (ratio 50:150) and potassium hydroxide (4.5 g, 5 eq.) was added. The reaction mixture was heated to reflux for 1 hour. 5. Upon completion of the reaction, the ethanol was removed by rotary evaporation and the solution was acidified with hydrochloric acid to pH 2. Subsequently, the aqueous solution was extracted with ethyl acetate (200 mL), the organic layer was separated, dried with magnesium sulfate and concentrated to give a white solid. 6. Finally, the white solid was recrystallized by dichloromethane and hexane to give 2 g of 2-propanoic acid-3-methylmaleic anhydride (80% yield).

[References]

[1] Patent: US9249179, 2016, B2. Location in patent: Page/Page column 35; 36
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