ChemicalBook CAS DataBase List GLUTACONIC ACID

GLUTACONIC ACID synthesis

10synthesis methods

Product Name:GLUTACONIC ACID
CAS Number:628-48-8
Molecular formula:C5H6O4
Molecular Weight:130.1

41527-39-3 Synthesis

41527-39-3
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628-48-8
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Yield:628-48-8 86%

Reaction Conditions:

with sodium hydroxide in water at 20; for 2.5 h;

Steps:

Preparation of trans-dibenzyl glutaconate
Dimethyl glutaconate (mixture of 83% trans and 17% cis, Fluka) was purified twice by flash chromatography on a silica column using solvent gradient 5%-20% ethyl acetate in hexane to obtain trans dimethyl glutaconate (>97%). Trans dimethyl glutaconate (10. 0243g, 0.063 mol) was dissolved in 100 ml H₂O and NaOH (5.8974 g, 0.147 mol) was added. The reaction mixture was stirred under room temperature for 2.5 hours and 10% sulfuric acid was added until pH <2.0. The resulting solution was extracted with ethyl acetate (3 x1 50 ml). The combined organic extracts were dried by Na₂SO₄, filtered and concentrated in vacuo, to give glutaconic acid (7.10 g, 0.055 mol, 86% yield) as white crystals. A 250 ml round bottom flask equipped with a Dean-Stark trap was charged with glutaconic acid (5.9156 g, 0.046 mol), benzyl alcohol (9.6 ml, 0.093 mol), toluene (60 ml) and TsOH·H2O (187.7 mg, 1 mmol). The stirred mixture was refluxed for 4 hours and then cooled to room temperature. Upon the removal of the solvent in vacuo, the residue was purified by chromatography on silica gel (hexane/EtOAc 9:1) to give trans-dibenzyl glutaconate (11.16 g, 0.036 mol, 79% yeild) as colorless oil.

References:

Wang, Wentian;Simovic, Dragan D.;Di, Mingping;Fieber, Lynne;Rein, Kathleen S. [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 7,p. 1949 - 1952] Location in patent:supporting information

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