DCC mediated esterification of 2,4-dinitrophenol; (S)-2’,4’-Dinitrophenyl 2-methylbutanoate
SyntheticPage 705
DOI:
10.1039/SP705
Submitted Nov 25, 2013, published Dec 03, 2013
Sergey Vatsadze (
zurabych@gmail.com), Alexey Medved'ko (
lexeym@gmail.com), Gregory Kazankov (
gkazankov@hotmail.com), Sergey Kurzeev (
kurzeev@gmail.com)
A contribution from
Vatsadze Group, Moscow State University
Chemicals Used
2,4-dinitrophenol (Labteh)
(S)-2-methylbutanoic acid (Sigma)
N,N-dicyclohexylcarbodiimide DCC (Sigma)
Ethyl acetate (Irea)
Petroleum ether 40-60°C (Irea)
Dichloromethane (Irea)
Silica gel
Procedure
2,4-dinitrophenol (0.4484 g, 2.44 mmol) and (S)-2-methylbutanoic acid (0.265 ml, 2.43 mmol) of were dissolved in dry ethyl acetate (4 ml) and cooled in ice bath. DCC (0.5074 g, 2.46 mmol) of was dissolved in dry ethyl acetate (4 ml) and was added to above solution in one portion under vigorous stirring. The reaction mixture was stirred for 1 h with cooling and 19 h at room temperature. The precipitated N,N-dicyclohexylurea was filtered off and the solvent was removed from the filtrate on rotary evaporator. The yellow oil thus obtained was purified with column chromatography. Eluent: petroleum ether:DCM:ethyl acetate 5:1:1. Product obatained as yellow oil that slowly solidifies in refrigerator. Yield 100% (650.1 mg).
Author's Comments
2,4-Dinitrophenyl ester elutes as the first yellow band, prior to 2,4-dinitrophenol.
Data
Yellow solid.
[α]d20 +16.6° (c 0.54, EtOAc).
1H-NMR (400MHz, CDCl3, δ, ppm): 1.05 (t, 3H, J 7.4Hz), 1.36 (d, 3H, 3J = 7Hz), 1.66 (dt, 1H, 3J = 14.1Hz, 3J = 7Hz), 1.9 (dt, 1H, 3J = 14.1 Hz, 3J = 7.2Hz), 2.75 (sext, 1H, 3J = 6.9Hz), 7.46 (d, 1H, 3J = 8.9Hz), 8.51 (dd, 1H, 3J = 8.9Hz, 3J = 2.7Hz), 8.94 (d, 1H, 3J = 2.6Hz).
Lead Reference
V. K. Kibirev, A. A. Gershkovich Sintez peptidov. Reagenty i metody (in Russian) // Kiev, 1987, p. 59.
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Keywords: alcohols, carboxylic acids, esters, nucleophilic, substitution