Synthesis of Ibuprofen Using Silica-Supported Preyssler Nanoparticles as an Eco-Friendly, Inexpensive, and Efficient Catalyst,
Organic Chemistry International
Volume 2014 (2014), Article ID 906801, 6 pages
Ali Gharib,1,2 Nader Noroozi Pesyan,3 Leila Vojdani Fard,4 and Mina Roshani1
1Department of Chemistry, Islamic Azad University, Mashhad, Iran
2Agricultural Researches and Services Center, Mashhad, Iran
3Department of Chemistry, Faculty of Science, Urmia University, Urmia 57159, Iran
4Education Organization of Razavi Khorasan, Education Ministry, Mashhad, Iran
Received 5 January 2014; Revised 15 February 2014; Accepted 31 March 2014; Published 6 May 2014
Academic Editor: Jonathan White
Copyright © 2014 Ali Gharib et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
This paper describes an alternative and simple procedure for the synthesis of Ibuprofen using Silica-Supported Preyssler Nanoparticles (H14[NaP5W30O110]/SiO2) (SPNPs), as an eco-friendly, inexpensive, and efficient catalyst. High yields, simplicity of operation, and easy work-up procedure are some advantages of this protocol. Silica-Supported Preyssler Nanoparticles (H14[NaP5W30O110]/SiO2) (SPNPs) offer the advantages of a higher hydrolytic and thermal stability. The salient features of Preyssler’s anion are availability, nontoxicity and reusability. We believe this methodology can find usefulness in organic synthesis.
Synthesis of Ibuprofen (6)
To a solution of ethyl-2-(4-isobutylphenyl) propanoate (1 g, 4.27 mmol) in 6 mL of CH3OH a solution of KOH was added (479 mg, 8.55 mmol) in 5 mL of H2O. The resultant solution was stirred at room temperature for 4 h. Methanol was removed under reduced pressure and the resulting solution was extracted with ethyl acetate and the organic extracts were washed with H2O, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give compound 6.
M.P (°C) 130-133,
IR (KBr, cm−1): 3100, 2920, 2870, 1716, 1408, 1419, 1321, 1230, 1184, 935, 779, 668, 583. 1H NMR (400 MHz, CDCl3) 7.15 (d, J = 8.1 Hz, 2H), 7.02 (d, J = 8.1 Hz, 2H), 3.64 (q, J = 7.2 Hz, 1H), 2.37 (d, J = 7.1 Hz, 2H), 1.75 (m, 1H), 1.43 (d, J = 7.1 Hz, 3H), 0.82 (d, J = 6.6 Hz, 6H).
13C NMR (100 MHz, CDCl3): 22.81, 22.82, 29.07, 42.64, 44.50, 128.80, 128.93, 128.95, 132.22, 140.23, 181.26. Anal. Calcd. for C13H18O2: C, 75.69; H, 8.80%. Found: C, 75.61; H, 8.70%.
HRMS (EI) Calcd. for C26H25FN4O6 [M]+, 206.1600, Found 206.1009.