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Preparation method of 2,5-dimethyl furan-3,4-dicarboxylate

A technology of diethyl diformate and dimethyl furan, which is applied in the field of preparation of organic compounds, can solve the problems of expensive reagents and high cost, and achieve the effects of simple and convenient operation, low cost and good application prospects

Inactive Publication Date: 2011-01-26
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have many problems such as the use of expensive reagents or toxic organic solvents, and the high cost.

Method used

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  • Preparation method of 2,5-dimethyl furan-3,4-dicarboxylate
  • Preparation method of 2,5-dimethyl furan-3,4-dicarboxylate
  • Preparation method of 2,5-dimethyl furan-3,4-dicarboxylate

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Experimental program
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Embodiment 1

[0019] Weigh 2,3-diacetylsuccinic acid diethyl ester (I) (243mg, 0.94mmol), add HCl solution (concentration: 0.4N, 3.3mL), heat and reflux under normal pressure microwave for 2 hours, cool to room temperature, diethyl ether Extract, collect the organic layer, wash with water and brine successively, dry over anhydrous sodium sulfate, filter, the filtrate recovers the solvent, and the residue is purified by flash column chromatography [eluting with petroleum ether-diethyl ether (5:1)] to obtain 2,5-Dimethylfuran-3-carboxylic acid ethyl ester (II) (colorless oil 51mg, yield 21%) and 2,5-dimethylfuran-3,4-dicarboxylic acid diethyl ester (IV ) (colorless oil 138mg, yield 61%).

[0020] Ethyl 2,5-dimethylfuran-3-carboxylate (II): 1 H NMR (CDCl 3 )δ: 1.33(t, 3H, J=7.1Hz), 2.36(s, 3H), 2.52(s, 3H), 4.26(q, 2H, J=7.1Hz), 6.21(s, 1H); 13 C NMR (CDCl 3 )δ: 13.2, 13.7, 14.5, 60.0, 106.3, 114.2, 150.0, 157.6, 164.4; consistent with literature reports (Wang Y et al. Org Lett, 2005, 7, 9...

Embodiment 2

[0023] Weigh 2,3-diacetylsuccinate diethyl (I) (184.7mg, 0.72mmol), add HCl solution (concentration: 1N, 1.2mL), heat and reflux under normal pressure microwave for 1 hour, cool to room temperature, diethyl ether Extract, collect the organic layer, wash with water and brine successively, dry over anhydrous sodium sulfate, filter, the filtrate recovers the solvent, and the residue is eluted by flash column chromatography [petroleum ether-diethyl ether (5:1) and then diethyl ether ] was purified to obtain ethyl 2,5-dimethylfuran-3-carboxylate (II) (colorless oil 24.0mg, yield 20%), 2,5-dimethylfuran-3,4- Dicarboxylic acid (III) (36.6mg of white crystals, yield 24%) and diethyl 2,5-dimethylfuran-3,4-dicarboxylate (IV) (90.0mg of colorless oil, yield 52%) ).

[0024] 2,5-Dimethylfuran-3,4-dicarboxylic acid (III): mp 214~216°; 1 H NMR (CD 3 COCD 3)δ: 2.60(s, 2×3H); 13 C NMR (CD 3 COCD 3 )δ: 14.5, 112.4, 161.5, 166.6; consistent with the measured data of commercially availabl...

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Abstract

The invention discloses a preparation method of 2, 5-dimethyl furan-3, 4-dioctyl phthalate diethyl ester, and the 2, 5-dimethyl furan-3, 4-dioctyl phthalate diethyl ester is prepared by a microwave heating refluxing reaction of 2, 3-diacetyl succinate diethyl ester in a hydrochloric acid solution with concentration of 0.1N to 1N. The preparation method has the advantages of no use of expensive reagents or toxic organic solvents, low cost, simple and convenient operation, applicability to industrialized production and the like; furthermore, 2, 5-dimethyl furan-3-ethyl formate and / or 2, 5-dimethyl furan-3, 4-dioctyl phthalate can be simultaneously obtained as required in a selective manner by the adjustment of the concentration of the hydrochloric acid solution; and the method has broad andgood application prospect.

Description

technical field [0001] The invention relates to a preparation method of an organic compound, in particular to a preparation method of 2,5-dimethylfuran-3,4-dicarboxylate diethyl. Background technique [0002] Polysubstituted furans are the pharmacodynamic structural units of many chemically synthesized drugs and natural drugs, and are also important intermediates in organic synthesis. Wherein, the derivative of trisubstituted furan---2,5-dimethylfuran-3-ethyl carboxylate has multiple biological activities, and can be used as wood preservative, bactericide, insecticide and fungicide (CN1152307A, 1997 ; JP 09255675A, 1997; DE 2323197, 1973) etc.; Tetrasubstituted furan - 2,5-dimethylfuran-3,4-dicarboxylic acid and 2,5-dimethylfuran-3,4-dicarboxylic acid di Ethyl esters are important chemical raw materials and pharmaceutical intermediates (Press JB et al.Eur J Med Chem, 1989,24,627; Nowak I et al.J.Fluorine Chem,1995,75,115; Gould KJ et al.J Chem Soc, Perkin Trans. 1, 1980, 1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/30
Inventor 何延红官智汪钢强
Owner SOUTHWEST UNIV