GLUTACONIC ACID synthesis
- Product Name:GLUTACONIC ACID
- CAS Number:628-48-8
- Molecular formula:C5H6O4
- Molecular Weight:130.1
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
471-25-0
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628-48-8
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32328-03-3
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628-48-8
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73192-75-3
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628-48-8
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16879-02-0
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628-48-8
65 suppliers
$20.00/100mg