Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 5
408
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Acylation of Aromatic Ethers Using Different Carboxylic Acid Anhydrides as Acylating Agents in the Presence of Nontoxic, Noncorrosive Resin Amberlyst 15 as a Solid Acid Catalyst

&
Pages 754-761 | Received 27 Aug 2009, Published online: 31 Jan 2011

REFERENCES

  • Harrington , P. J. ; Lodewijk , E. Twenty years of naproxen technology . Org. Process Res. Develop. 1997 , 1 , 72 – 76 .
  • Harvey , G. ; Mader , G. The shape–selective acylation of 2-methoxynaphthalene, catalyzed by zeolites Y, beta, and ZSM-12 . Collect. Czech Chem. Commun. 1992 , 57 , 862 – 868 .
  • Fujisawa , T. ; Kondo , K. ; Sakai , K. Process for preparing thiophene derivatives . US Patent , 4, 266, 067, 1981 .
  • Bradlow , L. H. ; Van der Werf , C. A. The preparation and chemical composition of difluoro-diphenyl-trichloroethane . J. Am. Chem. Soc. 1947 , 69 , 662 – 664 .
  • (a) Walker , H. G. ; Sanderson , J. J. ; Hauser , C. R. Acetoacetylation of aromatic compounds by boron fluoride to form β-diketones: Failure with boron and aluminum chlorides . J. Am. Chem. Soc. 1953 , 75 , 4109 – 4110 ; (b) Fodor , G. ; Kiss , J. ; Szekerke , M. J. Configuration of diastereoisomeric 3-methoxy-4-hydroxyphenylpropanolamines . J. Org. Chem. 1950 , 15 , 227 – 232 ; (c) Hyatt , J. A. ; Raynolds , P. W. Acyl fluoride Friedel–Crafts reactions: Regioselective synthesis of 3-acylacenaphthenes and 2-acyl-6-alkylnaphthalenes . J. Org. Chem. 1984 , 49 , 384 – 385 .
  • (a) Chiba , K. ; Arakawa , T. ; Tada , M. Synthesis of euglobal-G3 and -G4 . Chem. Commun. 1996 , 1763 – 1764 ; (b) Fujisawa , T. ; Ito , T. ; Fujimoto , K. ; Shimizu , M. ; Winberg , H. ; Staring , H. E. G. J. Facile synthesis of (S)-β-hydroxy-β-trichloromethylated aromatic ketones by the regioselective ring cleavage of chiral β-trichloromethyl-β-propiolactone under the Friedel–Crafts conditions . Tetrahedron Lett. 1997 , 38 , 1593 – 1596 ; (c) Bensari , A. ; Zaveri , N. T. Titanium(IV) chloride–mediated ortho-acylation of phenols and naphthols . Synthesis 2003 , 267 – 271 .
  • Paul , S. ; Nanda , P. ; Gupta , R. ; Loupy , R. A. Zinc-mediated Friedel–Crafts acylation in solvent-free conditions under microwave irradiation . Synthesis 2003 , 2877 – 2881 .
  • Mukaiyama , T. ; Nagaoka , H. ; Ohshima , M. ; Murakami , M. The diphenylboryl hexachloroantimonate–promoted Friedel–Crafts acylation reaction . Chem. Lett. 1986 , 165 – 168 .
  • Chao , H. ; Matsuki , S. ; Mizuno , A. ; Annoura , H. ; Tatsuoka , T. Synthesis of pyrroloazepines: Facile synthesis of 2-substituted pyrrole derivatives by the phosgene method . J. Heterocycl. Chem. 1997 , 34 , 87 – 91 .
  • Yamoto , T. ; Hideshama , C. ; Prakash , G. K. S. ; Olah , G. A. Organic reactions catalyzed by solid superacids: Perfluorinated sulfonic acid resin (Nafion-H)–catalyzed intramolecular Friedel–Crafts acylation . J. Org. Chem. 1991 , 56 , 3955 – 3957 .
  • Effenberger , F. ; Eppel , G. Katalytische Friedel–Crafts Acylierung von Aromaten . Angew. Chem. 1972 , 84 , 295 – 296 .
  • Anderson , K. W. ; Tepe , J. J. Trifluoromethanesulfonic acid–catalyzed Friedel–Crafts acylation of aromatics with β-lactams . Tetrahedron 2002 , 58 , 8475 – 8481 .
  • Akiko , O. ; Katsuya , M. ; Hideki , O. ; Noriyuki , Y. Electrophilic aromatic aroylation with CF3-bearing arenecarboxylic acid derivatives: Reaction behavior and acidic mediator dependence . Synth. Commun. 2007 , 37 , 2701 – 2715 .
  • Olah , G. A. Friedal–Crafts Chemistry ; Wiley/Interscience : New York , 1973 .
  • Eaton , P. E. ; Carlson , G. R. ; Lee , J. T. Phosphorus pentoxide–methanesulfonic acid: Convenient alternative to polyphosphoric acid . J. Org. Chem. 1973 , 38 , 4071 .
  • Simons , J. H. Hydrogen fluoride catalysis. Adv. Catal. 1950, 2, 197–232.
  • (a) Olah , G. A. Friedel–Crafts and Related Reactions ; Wiley-Interscience : New York , 1963–1964 ; vols. 1–4 ; (b) Olah , G. A. Friedel–Crafts Chemistry ; Wiley/Interscience : New York , 1973 ; (c) Hattori , H. Heterogeneous Catalysis and Fine Chemical III ; Elsevier : Amsterdam , 1993 .
  • (a) Corma , A. Inorganic solid acids and their use in acid-catalyzed hydrocarbon reactions . Chem. Rev. 1995 , 95 , 559 – 614 ; (b) Sartori , G. ; Maggi , R. Use of solid catalysts in Friedel–Crafts acylation reactions . Chem. Rev. 2006 , 106 , 1077 – 1104 ; (c) Waghmare , N. G. ; Kasinathan , P. ; Amrute , A. ; Lucas , N. ; Halligudi , S. B. Titania-supported silicotungstic acid: An efficient solid acid catalyst for veratrole acylation . Catal. Commun. 2008 , 9 , 2026 – 2029 .
  • (a) Spagnol , M. ; Gilbert , L. ; Guillot , H. ; Tirel , P. J. Acylation method for an aromatic compound. PCT WO Patent 97/48665, 1997 ; (b) Metivier , T. In Fine Chemicals through Heterogeneous Catalysis ; R. A. Sheldon , H. van Bekkum ( Eds. ); Wiley-WCH : Weinheim , 2001 ; p. 161 .
  • Rohan , D. ; Canaff , C. ; Fromentin , E. ; Guisnet , M. Acetylation of anisole by acetic anhydride over a HBEA zeolite—Origin of deactivation of the catalyst . J. Catal. 1998 , 177 , 296 – 305 .
  • Derouane , E. G. ; Dillon , C. J. ; Bethell , D. ; Derouane-Abd Hamid , S. B. Zeolite catalysts as solid solvents in fine chemicals synthesis: Catalyst deactivation in the Friedel–Crafts acetylation of anisole . J. Catal. 1999 , 187 , 209 – 218 .
  • Moreau , P. ; Finiels , A. ; Meric , P. Acetylation of dimethoxybenzenes with acetic anhydride in the presence of acidic zeolites . J. Mol. Catal. 2000 , 154 , 185 – 192 .
  • (a) Harmer , M. A. Industrial processes using solid acid catalysts . In Handbook of Green Chemistry and Technology ; J. H. Clark , D. J. Macquarris ( Eds. ); Blackwell : London , 2002 ; p. 86 ; (b) Patil , S. B. ; Singh , P. R. ; Surpur , M. P. ; Samant , S. D. Cation-exchanged resins: efficient heterogeneous catalysts for facile synthesis of 1-amidoalkyl-2-naphthols from one-pot, three-component condensations of amides/ureas, aldehydes, and 2-naphthol. Synth. Commun. 2007, 37, 1659–1664 ; (c) Surpur , M. P. ; Singh , P. R. ; Patil , S. B. ; Samant , S. D. Expeditious one-pot and solvent-free synthesis of dihydroquinazolin-4(1H)-ones in the presence of microwaves. Synth. Commun. 2007, 37, 1965–1970 ; (d) Chakrabarti , A. ; Sharma , M. M. Cationic ion exchange resins as catalyst. React. Polym. 1993, 20, 1–45 .
  • Kobayashi , S. ; Komoto , I. Remarkable effect of lithium salts in Friedel–Crafts acylation of 2-methoxynaphthalene catalyzed by metal triflates . Tetrahedron 2000 , 56 , 6463 – 6465 .
  • Mellor , J. M. ; Mittoo , S. ; Parkes , R. ; Millar , R. W. Improved nitrations using metal nitrate–sulfuric acid systems . Tetrahedron 2000 , 56 , 8019 – 8024 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.