ChemicalBook CAS DataBase List ETHYL 4-(2-NITROPHENYL)ACETOACETATE

ETHYL 4-(2-NITROPHENYL)ACETOACETATE synthesis

9synthesis methods

Product Name:ETHYL 4-(2-NITROPHENYL)ACETOACETATE
CAS Number:66073-33-4
Molecular formula:C12H13NO5
Molecular Weight:251.24

1,3-Dioxane-4,6-dione, 5-[1-hydroxy-2-(2-nitrophenyl)ethylidene]-2,2-dimethyl-

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Yield:66073-33-4 100%

Reaction Conditions:

in ethanol; for 5 h;Reflux;

Steps:

2.2.2. Synthesis of ethyl 4-(2-nitrophenyl)-3-oxobutanoate (5)

307 mg (1 mmol) of compound 4 was dissolved in 20 mL of ethanol,and the solution was refluxed for 5 h. After completion of the reaction,monitored by TLC, the solvent was removed. The crude product wasadded 50 mL of water and extracted by EtOAc (3 × 30 mL). The combinedorganic phases were washed with brine and then dried with MgSO4. Evaporation of the solvent gave the crude product, which waspurified by column chromatography eluted by hexane:EtOAc (5:1)mixture yield the ethyl 4-(2-nitrophenyl)-3-oxobutanoate (5) quantitativelyas the white crystals. m.p.: 58 - 60 C. 1H NMR (400 MHz, CDCl3) 8.16 (d, J = 8.2 Hz, 1H), 7.63 (t, J = 7.4 Hz, 1H), 7.50 (t, J = 7.8 Hz,1H), 7.34 (d, J = 7.5 Hz, 1H), 4.28 (s, 2H), 4.25 (q, J = 7.5 Hz, 2H), 3.66(s, 2H), 1.32 (t, J = 7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) 198.3,167.0, 148.4, 133.8, 133.7, 129.6, 128.7, 125.2, 61.5, 49.2, 47.7, 14.1.

References:

Ayd?n, Hatice Gülten;Ekmekci, Zeynep;Kaya, Serdal;Keskin, Selbi;Menges, Nurettin [Journal of Photochemistry and Photobiology A: Chemistry,2021,vol. 420,art. no. 113487]

141-97-9 Synthesis