Microwave Synthesis of (4-hydroxy Phenyl) 3-oxo butanoate
Mohammed Ramdani *, Nour-Eddine Benchat, Abderrahmane Anaflous, Fouad El Kalai
Applied Chemistry and Environement Laboratory, Faculty of Sciences, Univerity Mohamed 1st, Oujda, Morooco
*
Author to whom correspondence should be addressed. Fax : +212 36 50 06 03; E-Mail: [email protected]
Received: 2 May
2007; in revised form: 20 November 2007
/ Accepted: 15 January 2008 / Published: 25 March 2008
The product 3 was previously prepared [1]
using C6H6 in the presence of pyridine.
A mixture
of hydroquinone 1 (0.66
g, 6 mmol), ethyl acetoacetate 2 (0.78 g, 6 mmol) and
monmorillonite K10 (0.43 g,
30 % by weight of the total reactants) [2,3] was placed in a pyrex tube which
was then introduced into a Maxidigest MX 350 Prolabo microwave monomode reactor
fitted with a rotational system [4]. An approximate final temperature (120 °C) was measured by
introducing a digital thermometer at the end of the irradiation time (20 min on
180 W as irradiation power). The mixture was cooled to
ambient temperature. After
elution with ethyl acetate (30 mL) and subsequent filtration through florisil,
the organic product was purified by chromatography on silicagel
(dichloromethane : ethyl acetate, 90 :10), yield : 65 % of 3
white solid.
Melting point: 96-98 °C.
1H NMR d (CDCl3, 200 MHz): 7-6.7 (2d, 4H,
Ph); 5,65 (s, OH) ; 3.7 (s, CH2); 2.38 (s, CH3).
13C NMR d (CDCl3, 100 MHz): 30 (CH3);
50 (CH2); 116 and 123 (C=C arom.); 155 (CO2); 202 (C=O
acyl).
MS (IC-NH3,
m / z): 212(M+ + 18) / 100 %.
References
- Rall, K.B.; Perekalin, V.V. Zhurnal
Obshchei Khimii 1955, 25, 259.
- Li, T.S.; Zhang, Z.H.; Yang, F.; Fu, C.G. J. Chem. Research (S) 1998, 38-39.
- Singh, J.; Kaur, J.; Nayyar, S.;
Kad, G.L. J. Chem. Research (S) 1998, 280-281.
- (a) Kappe, C.O.; Dallinger, D. Nature Reviews
Drug Discovery 2006, 5, 51; (b) De la Hoz, A.; Diaz-Ortiz,
A.; Moreno, A. Chem. Soc. Rev., 2005, 34, 164.
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2008 by MDPI (http://www.mdpi.org/).
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