Uses
Dimethyl glutaconate may be used in the synthesis of:
- dimethyl 3-[(Z)-1-propenyl]glutarate
- phenanthridinone derivatives
- substituted benzenes
General Description
Dimethyl glutaconate, also known as dimethyl 2-pentenoate, is a diester. It reacts with salicaldehyde in the presence of piperidine to form a coumarin-fused electron deficient diene.
Synthesis
Methanol (10.0 kg, 3.1 kmol), pent-2-enoic acid (5.57 kg, 0.043 kmol), and concentrated sulfuric acid (72.0 g) were sequentially added to a 20 L enameled reactor equipped with a mechanical stirrer and a thermometer. The reaction mixture was heated to reflux for the reaction. After completion of the reaction, methanol was recovered by distillation under reduced pressure. After the temperature was lowered to 20 °C, the reaction solution was washed with aqueous sodium carbonate to neutralize the acid and subsequently dried. Finally, the product was purified by vacuum distillation to give 6.22 kg of colorless liquid dimethyl pent-2-enoate in 91.5% yield and 81.6% total yield. The product was analyzed by gas chromatography (GC) with a purity of 98.8% (22.4% cis-isomer and 76.4% trans-isomer).
References
[1] Chemical Communications, 2015, vol. 51, # 77, p. 14505 - 14508
[2] Patent: CN108358783, 2018, A. Location in patent: Paragraph 0032; 0035
[3] Tetrahedron, 1992, vol. 48, # 46, p. 10103 - 10114
