Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 8
120
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Tetrahydropyranylation of Phenols and Alcohols Catalyzed by Supported Mo and W Keggin Heteropolyacids

, , , , &
Pages 1359-1365 | Received 15 Jun 2002, Published online: 15 Aug 2006

References

  • Greene , T.W. and Wuts , P.G.M. 1991 . “ Protection for the hydroxyl group, including 1,2- and 1,3-diols ” . In Protective Groups in Organic Synthesis: Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols, , 2nd Ed. 31 – 34 . New York : Wiley .
  • McOmie , J.F.W. 1963 . Protective groups . Adv. Org. Chem. , 3 : 191 – 294 .
  • Heravi , M.M. , Ajami , D. and Ghassemzadeh , M. 1999 . Solvent free tetrahydropyranylation of alcohols and phenols over sulfuric acid adsorbed on silica gel . Synth. Commun. , 29 ( 6 ) : 1013 – 1016 .
  • Ranu , B.C. and Saha , M.A. 1994 . Simple, efficient, and selective method for tetrahydropyranylation of alcohols on a solid phase of alumina impregnated with zinc chloride . J. Org. Chem. , 59 : 8269 – 8270 .
  • Choudary , B.M. , Neeraja , V. and Lakshmi Kantam , M. 2001 . Vanadyl(IV) acetate: a mild and efficient heterogeneous catalyst for the tetrahydropyranylation of alcohols, thiols and phenols . J. Mol. Catal. A—Chemical , 175 : 169 – 172 .
  • Curini , M. , Epifano , F. , Marcotullio , M.C. , Rosati , O. and Costantino , U. 1998 . Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in tetrahydropyranylation of alcohols and phenols . Tetrahedron Lett. , 39 : 8159 – 8162 .
  • Kozhevnikov , I.V. 1995 . Heteropoly acids and related compounds as catalysts for fine chemical synthesis . Catal. Rev. Sci. Engin. , 37 ( 2 ) : 311 – 352 .
  • Pizzio , L.R. , Cáceres , C.V. and Blanco , M.N. 1998 . Acid catalysts prepared by impregnation of tungstophosphoric acid solutions on different supports . Appl. Catal. A , 167 ( 2 ) : 283 – 294 .
  • Vázquez , P.G. , Blanco , M.N. and Cáceres , C.V. 1999 . Catalysts based on supported 12-molybdophosphoric acid . Catal. Lett. , 60 : 205 – 215 .
  • The silica-supported MPA or TPA based catalysts were prepared by means of the pore filling impregnation technique . Solutions of H3PMo12O40·n H2O (MPA) or H3PW12O40·n H2O (TPA) in ethanol-water were used with the necessary concentration in order to obtain a content of 0.3 g MPA(TPA)/g catalyst. The support was SiO2 Grace (S). Then, the catalysts were dried at room temperature for 24 h and calcined at 250°C for 1 h
  • Okuhara , T. , Mizuno , N. and Misono , M. 1996 . Catalytic chemistry of heteropoly compounds . Adv. Catal. , 41 : 113 – 252 .
  • Molnár , A. and Beregszászi , T. 1996 . Mild and efficient tetrahydropyranylation and deprotection of alcohols catalyzed by heteropoly acids . Tetrahedron Lett , 37 ( 47 ) : 8597 – 8600 .
  • Grant , H.N. , Prelog , V. and Sneeden , R.P.A. 1963 . Synthese eines 1-oxaphenalen-derivates mit dem chromophoren system des biflorins . Helv. Chim. Acta , 46 : 415 – 421 .
  • The used catalysts, MPA and TPA both supported on silica, were prior to the reaction, washed with toluene three times during 24 h each, with continuous stirring. The final content of HPA showed to be 0.3 mg MPA(TPA)/mg of catalyst
  • Analytical data for selected acetals: 1—THP: Calcd. for C11H14O2: C, 74.13, H, 7.92. Found: C, 74.01, H, 7.90. 2—THP: Calcd. for C11H13NO4: C, 59.19, H, 5.87, N, 6.27. Found: C, 59.23, H, 5.85, N, 6.24. 4—THP: Calcd. for C12H16O3: C, 69.21, H, 7.74. Found: C, 69.16, H, 7.72. 5—THP: Calcd. for C15H22O2: C, 76.87, H, 9.48. Found: C, 76.81, H, 9.44. 8—THP: Calcd. for C15H16O2: C, 78.92, H, 7.06. Found: C, 78.87, H, 7.03. 10—THP: Calcd. for C13H18O2: C, 75.69, H, 8.80. Found: C, 75.62, H, 8.78. 11—THP: Calcd. for C14H20O2: C, 76.32, H, 9.15. Found: C, 76.25, H, 9.12. 13—THP: Calcd. for C13H18O3: C, 70.24, H, 8.16. Found: C, 70.19, H, 8.12

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.