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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 19
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Original Articles

Green Oxidation of Methylarenes to Benzoic Acids with Bromide/Bromate in Water

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Pages 2922-2929 | Received 10 Jul 2009, Published online: 25 Aug 2010

REFERENCES

  • (a) Sheldon , R. A. ; Kochi , J. K. Metal-Catalyzed Oxidations of Organic Compounds ; Academic Press : New York , 1981 ; (b) Cainelli , G. ; Cardillo , G. Chromium Oxidations in Organic Chemistry ; Springer : Berlin , 1984 ; (c) Hudlicky , M. Oxidations in Organic Chemistry ; American Chemical Society : Washington , DC , 1990 ; (d) Hirabayashi , T. ; Sakaguchi , S. ; Ishii , Y. A new route to lactam precursors from cycloalkanes: Direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-butyl nitrite and N-hydroxyphthalimide. Angew. Chem. Ind. Ed. 2004, 43, 1120–1123 ; (e) Suresh , A. K. ; Sharma , M. M. ; Sridhar , T. Engineering aspects of industrial liquid-phase air oxidation of hydrocarbons. Ind. Eng. Chem. Res. 2000, 39, 3958–3997 .
  • (a) Wiberg , K. B. In Oxidation in Organic Chemistry ; K. B. Wiberg (Ed.); Academic Press : New York , 1965 ; part A , p. 69 ; (b) March , J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, , 4th ed. ; John Wiley & Sons : New York , 1992 .
  • Sam , D. J. ; Simmons , H. E. Crown polyether chemistry: Potassium permanganate oxidations in benzene . J. Am. Chem. Soc. 1972 , 94 , 4024 – 4025 .
  • Friedman , L. ; Fishel , D. L. ; Shechter , H. Oxidation of alkylarenes with aqueous sodium dichromate dichromate: A useful method for preparing mono- and polyaromatic carboxylic acids . J. Org. Chem. 1965 , 30 , 1453 – 1457 .
  • (a) Muzart , J. Chromium(VI) complex catalyzed benzylic oxidations in the presence of tert-butyl hydroperoxide . Tetrahedron Lett. 1986 , 27 , 3139 – 3142 ; (b) Muzart , J. Practical chromium(VI) oxide–catalyzed benzylic oxidations using 70% tert-butylhydroperoxide . Tetrahedron Lett. 1987 , 28 , 2131 – 2132 ; (c) Yamazaki , S. Chromium(VI) oxide–catalyzed benzylic oxidation with periodic acid . Org. Lett. 1999 , 1 , 2129 – 2132 .
  • (a) Bastock , T. W. ; Clark , J. H. ; Matin , K. ; Trenbirth , B. W. Mild, solvent-free oxidation of toluene and substituted toluenes to their benzoic acids using carboxylic acid–promoted heterogeneous catalysis . Green Chem. 2002 , 4 , 615 – 617 ; (b) Sasson , Y. ; Zappi , G. D. ; Neumann , R. Liquid-phase oxidation of deactivated methylbenzenes by aqueous sodium hypochlorite catalyzed by ruthenium salts under phase-transfer catalytic conditions . J. Org. Chem. 1986 , 51 , 2880 – 2883 ; (c) Saha , B. ; Espenson , J. H. Combined acid additives and the MC catalyst for the autoxidation of p-xylene to terephthalic acid . J. Mol. Catal. A: Chem. 2005 , 241 , 33 – 38 , and the references therein ; (d) Bonvin , Y. ; Callens , E. ; Larrosa , I. ; Henderson , D. A. ; Oldham , J. ; Burton , A. J. ; Barrett , A. G. M. Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide . Org. Lett. 2005 , 7 , 4549 – 4552 ; (e) Shaikh , T. M. ; Emmanuvel , L. ; Sudalai , A. NaIO4-mediated selective oxidation of alkylarenes and benzylic bromides/alcohols to carbonyl derivatives using water as solvent . J. Org. Chem. 2006 , 71 , 5043 – 5046 .
  • Yoshino , Y. ; Hayashi , Y. ; Iwahama , T. ; Sakaguchi , S. ; Ishii , Y. Catalytic oxidation of alkylbenzenes with molecular oxygen under normal pressure and temperature by N-hydroxyphthalimide combined with Co(OAc)2 . J. Org. Chem. 1997 , 62 , 6810 – 6813 .
  • Shaikh , T. M. ; Sudalai , A. WO3/70% TBHP/aqueous NaOH: An efficient catalytic combination for the selective oxidation of methylarenes and alkyl aryl ketones to benzoic acids . Eur. J. Org. Chem. 2008 , 4877 – 4880 .
  • (a) Adimurthy , S. ; Ramachandraiah , G. ; Bedekar , A. V. ; Ghosh , S. ; Ranu , B. C. ; Ghosh , P. K. Eco-friendly and versatile brominating reagent prepared from liquid bromine precursor . Green Chem. 2006 , 8 , 916 – 922 ; (b) Adimurthy , S. ; Ghosh , S. ; Patoliya , P. U. ; Ramachandraiah , G. ; Agrawal , M. K. ; Gandhi , M. R. ; Upadhyay , S. C. ; Ghosh , P. K.; Ranu, B. C. An alternative method for the regio- and stereoselective bromination of alkenes, alkynes, toluene derivatives, and ketones using a bromide/bromate couple B. C . Green Chem. 2008 , 10 , 232 – 237 .
  • (a) Clarke , H. T. ; Taylor , E. R. Preparation of o-chlorobenzoicacid . Org. Synth. 1943 , 2 , 135 – 136 ; (b) Blum , J. ; Rosenman , H. ; Bergmann , E. D. Oxidation of alkylbenzenes, catalyzed by chlorotris(triphenylphosphine)rhodium . Tetrahedron Lett. 1967 , 8 , 3665 – 3668 ; (c) Kurkov , V. P. ; Pasky , J. Z. ; Lavigne , J. B. The free-radical nature of chlorotris(triphenylphosphine)rhodium-catalyzed autoxidations of cyclohexene and ethylbenzene . J. Am. Chem. Soc. 1968 , 90 , 4743 – 4744 .
  • (a) Sidheswaran , M. ; Tavlarides , L. L. Visible light photocatalytic oxidation of toluene using a cerium-doped titania catalyst . Ind. Eng. Chem. Res. 2008 , 47 , 3346 – 3357 ; (b) Amati , A. ; Dosualdo , G. ; Zhao , L. ; Bravo , A. ; Fontana , F. ; Minisci , F. ; Bjorsvik , H. R. Catalytic processes of oxidation by hydrogen peroxide in the presence of Br2 or HBr: Mechanism and synthetic applications . Org. Process Res. Dev. 1998 , 2 , 261 – 269 .
  • Pauchert , C. J. ; Behnke , J. The Aldrich Library of 13C and 1H FT NMR Spectra, , 1st ed. ; Aldrich : Madison , WI , 1993 , vol. 2 .
  • Sheibley , F. E. ; Mcnulty , J. S. 3,5-Dichloroaniline in Sandmeyer's isatin synthesis: 4,6-Dichloroanthranilic acid . J. Org. Chem. 1956 , 21 , 171 – 173 .
  • Sayed , S. β-Aroyl-α- and -β-arylpropionic acids, part 1: Their preparation and lactonization . Can. J. Chem. 1961 , 39 , 2563 – 2571 .

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