1,5-Dimethyl 2-pentenedioate

To a 20 L enamel reactor equipped with a stirring and a thermometer, methanol (10.0 kg, 3.1 kmol), glutaconic acid (5.57 kg, 0.043 kmol), concentrated sulfuric acid (72.0 g) were added, and the mixture was heated under reflux for 4 hours.After the reaction is completed, the methanol is recovered under reduced pressure, and the temperature is lowered to 20 ° C, and the obtained liquid is respectively water, The sodium carbonate aqueous solution was washed, dried, and vacuum distillation to obtain 6.22 kg of a colorless liquid dimethyl glutaconate, the yield was 91.5percent, the total yield was 81.6percent, and the content was 98.8percent (GC test, cis 22.4percent, anti- Formula 76.4percent).Under an atmosphere of nitrogen, 1.2 mL (22.3 mmol, 0.05 equivalents) of sulfuric acid (Fluka) was added to 80 g (0.42 mol, 1.0 equivalent) dimethyl 3-methoxyglutarate, as obtained in or 2, in a distillation apparatus with round-bottomed flask. The mixture was slowly heated to 165 °C, and the methanol formed was directly distilled off. After 7 hours, heating was stopped and the residue in the flask was mixed with a saturated solution of sodium hydro gencarbonate. After removal of the organic phase, the aqueous phase was washed three times with 50 mL diethyl ether each. Then, the organic phases were combined, washed with 250 mL brine, and distilled under reduced pressure. The yield was 45.9 g (69percent) of dimethyl glutaconate (bp

Molecular Weight:158.15
XLogP3:0.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:158.05790880
Monoisotopic Mass:158.05790880
Topological Polar Surface Area:52.6
Heavy Atom Count:11
Complexity:171
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes