Download PDF
Synlett 2010(17): 2644-2648  
DOI: 10.1055/s-0030-1258580
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Step Oxidation of 2-Arylpropanols to 2-Arylpropionic Acids: Improving Sustainability in the Synthesis of Profens

Paola Galletti, Matteo Pori, Daria Giacomini*
Department of Chemistry, ‘G. Ciamician’ University of Bologna, Via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: daria.giacomini@unibo.it;
Further Information

Publication History

Received 28 July 2010
Publication Date:
23 September 2010 (online)

   Permissions and Reprints All articles of this category

Abstract

Three oxidation procedures were evaluated for the synthesis of optically pure 2-arylpropionic acids. Efficient, mild, and eco-friendly conditions were obtained with the system comprising TEMPO, NaClO, and NaClO2. Thus a series of profens were obtained in good to excellent yields.

Key words

oxidation - alcohols - carboxylic acids - anti-inflammatory agents - profens - TEMPO

    References and Notes

  • 1 Ley SV. Madfin A. In Comprehensive Organic Synthesis   Vol. 7:  Trost BM. Fleming I. Ley SV. Pergamon; Oxford: 1991.  p.251 
    Search in Google Scholar
  • 2 Cainelli G. Cardillo G. Chromium Oxidations in Organic Chemistry   Springer; Berlin: 1984. 
  • 3a Arends WCE. Sheldon RA. In Modern Oxidation of Alchols using Environmentally Benign Oxidants, In Modern Oxidation Methods   Bäckvall J.-E. Wiley-VCH; Weinheim: 2004.  p.83 
  • 3b ten Brink GJ. Arends IWCE. Sheldon RA. Science  2000,  287:  1636 
    Search in Google Scholar
  • 4 Noyori R. Aoki M. Sato K. Chem. Commun.  2003,  1977 
    Crossref
  • For reviews of TEMPO-catalyzed alcohol oxidations, see:
  • 5a de Nooy AEJ. Besemer AC. van Bekkum H. Synthesis  1996,  1153 
  • 5b Adam W. Saha-Möller CR. Ganeshpur PA. Chem. Rev.  2001,  101:  3499 
    Search in Google Scholar
  • 5c Sheldon RA. Arends IWCE. ten Brink G.-J. Dijksman A. Acc. Chem. Res.  2002,  35:  774 
    Search in Google Scholar
  • 5d Sheldon RA. Arends IWCE. Adv. Synth. Catal.  2004,  346:  1051 
    Search in Google Scholar
  • 5e Vogler T. Studer A. Synthesis  2008,  1979 
  • 6a Giacomini D. Galletti P. Quintavalla A. Gucciardo G. Paradisi F. Chem. Commun.  2007,  4038 
  • 6b Giacomini D, Cainelli G, Galletti P, Gucciardo G, and Quintavalla A. inventors; WO  2008074717. 
  • 6c Galletti P. Emer E. Gucciardo G. Quintavalla A. Pori M. Giacomini D. Org. Biomol. Chem.  2010,  8:  4117 
    Search in Google Scholar
  • 7a Li X. List B. Chem. Commun.  2007,  1739 
  • 7b Cleij M. Archelas A. Furstoss R. J. Org. Chem.  1999,  64:  5029 
    Search in Google Scholar
  • 8 Basak A. Nag A. Bhattacharya G. MandalS . Nag S. Tetrahedron: Asymmetry  2000,  11:  2403 ; and references cited therein
    CrossrefSearch in Google Scholar
  • 10 Fernandes RA. Kumar P. Tetrahedron Lett.  2003,  44:  1275 
    CrossrefSearch in Google Scholar
  • 11 RebeloS LH. Simões MMQ. Neves MGPMS. Cavaleiro JAS. J. Mol. Catal. A: Chem.  2003,  201:  9 
    CrossrefSearch in Google Scholar
  • 12 Baciocchi E. Belvedere S. Bietti M. Tetrahedron Lett.  1998,  39:  4711 
    CrossrefSearch in Google Scholar
  • 13 Tokunaga M. Aoyama H. Shirogane Y. Obora Y. Tsuji Y. Catal. Today  2006,  117:  138 
    CrossrefSearch in Google Scholar
  • 14a Zhao M. Li J. Mano E. Song Z. Tschaen DM. Grabowski EJJ. Reider PJ. J. Org. Chem.  1999,  64:  2564 
    Search in Google Scholar
  • 14b Zhao M. Li J. Mano E. Song ZJ. Tschaen DM. Org. Synth.  2005,  81:  195 
    Search in Google Scholar
  • 16 Cann MC. Connelly ME. The BHC Company Synthesis of Ibuprofen, In Real-World Cases in Green Chemistry   American Chemical Society; Washington DC: 2000. 
  • 17 Röben C. Studer A. Hemme WL. Eckert H. Synlett  2010,  1110 ; and references cited therein
    Thieme Connect
  • 18 Figiel PJ. Sibaouih A. Ahmad JU. Nieger M. Räisänen MT. Leskelä M. Repo T. Adv. Synth. Catal.  2009,  351:  2625 
    CrossrefSearch in Google Scholar
9

Compounds 1b-g were obtained by BH3˙SMe2 reduction from commercially available racemic acids. Compound 1h was easily obtained in a three steps synthesis starting from ketoprofen (EtOH, BF3˙OEt2 cat.; ethylene glycol, TsOH cat. in toluene; LiAlH4 in THF).

15

Referred to reported data, see ref. 7.