Dimethyl itaconate

Chemical Properties

white crystalline low melting mass or liquid

Uses

Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.

Uses

Dimethyl itaconate may be used in functionalization of isotactic poly(propylene). It was used in crosslinking of polyesters: poly(isosorbide itaconate)and poly(isosorbide itaconate-co-succinate).

Uses

Dimethyl Itaconate is a chemical reagent used in the synthesis of functionalized 2-isoxazolines used in fragment-based drug discovery.

General Description

Dimethyl itaconate undergoes enantioselective Rh(I)-catalyzed hydrogenation which can be enhanced by appropriate choice of substituents on aromatic ring of (1,2-diarylphosphinoxy)cyclohexane.

Flammability and Explosibility

Non flammable

Synthesis

1. Itaconic acid, methanol and catalyst were mixed in a certain ratio and transferred to a 100 mL autoclave. 2. The reaction mixture was continuously stirred at 120 °C. 3. Optimization of the reaction conditions was carried out by adjusting the parameters such as the molar ratio of methanol to itaconic acid, the catalyst dosage and the reaction time. 4. Upon completion of the reaction, the catalyst was separated and recovered through a filtration operation.

Purification Methods

Crystallise the ester from MeOH by cooling to -78o. [Beilstein 2 IV 2229.]

References

[1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 368-369, p. 24 - 30
[2] Heterocycles, 1988, vol. 27, # 8, p. 1887 - 1898
[3] Tetrahedron Letters, 2015, vol. 56, # 27, p. 4119 - 4123
[4] Chemistry and physics of lipids, 2002, vol. 120, # 1-2, p. 9 - 20
[5] Russian Chemical Bulletin, 2005, vol. 54, # 2, p. 348 - 353