Download PDF
Synthesis 2001(7): 1093-1097
DOI: 10.1055/s-2001-14569
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile, Selective Preparation of Monoketals from Pentaerythritol and Ketones

Marcelo C. Murguía, Santiago E. Vaillard, Ricardo J. Grau*
Instituto de Desarrollo Tecnológico para la Industria Química (INTEC), Universidad Nacional del Litoral and CONICET Güemes 3450, (3000) Santa Fe, Argentina
Fax: +54(342)4551918; e-Mail: cqfina@ceride.gov.ar;
Further Information

Publication History

Received 14 November 2000
Publication Date:
30 September 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

The selective preparation of monoketals 3a-f from pentaerythritol 1 and cyclic, acyclic, aromatic, and aliphatic ketones 2a-f was achieved by a facile method. The extreme polarity and low solubility of pentaerythritol in almost all organic solvents were the main difficulties to be overcome for the preparation of monoketals in good yields and high selectivity. A benzene-dimethylformamide (40:60) mixture proved to be excellent for the ketalization. The one-step procedure developed allowed the preparation of monoketals in good yields and good to excellent selectivity (higher than 90%).

Key words

pentaerythritol - 1,3-diols - monoketals - monoprotection - 1,3-dioxanes

    References

  • 1a

    Research Assistant from CONICET

  • 1b

    Research Assistant from U. N. L

  • 1c

    Professor at U. N. L. and Member of CONICET’s Research Staff

  • 2 Meskens FAJ. Synthesis  1981,  501 
    Article in Thieme ConnectGoogle Scholar
  • 3 Schelhaas M. Waldmann H. Angew. Chem., Int. Ed. Engl.  1996,  35:  2056 
    CrossrefGoogle Scholar
  • 4 Brown JJ. Lenhard RH. Berstein S. J. Am. Chem. Soc.  1964,  86:  2183 
    CrossrefGoogle Scholar
  • 5 Coe JW. Roush WR. J. Org. Chem.  1989,  54:  915 
    CrossrefGoogle Scholar
  • 6a Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   2nd ed.:  Wiley; New York: 1991.  p.68-86  
    Google Scholar
  • 6b Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   2nd ed.:  Wiley; New York: 1991.  p.178-198  
    Google Scholar
  • 7 Tanaka N. Masaki Y. Synlett  1999,  12:  1960 
    Article in Thieme ConnectGoogle Scholar
  • 8 Zhu Y. Masuyama A. Kirito Y. Okahara M. Rosen M. J. Am. Oil Chem. Soc.  1992,  69:  626 
    Google Scholar
  • 9 Kim T.-S. Hirao T. Ikeda I. J. Am. Oil Chem. Soc.  1996,  73:  67 
    Google Scholar
  • 10 Conrad WE. Gesner BE. Levasseur LA. Murphy RF. Conrad HM. J. Org. Chem.  1961,  26:  3571 
    Google Scholar
  • 11 Schenieder G. Kovács . Chironai M. Acta Phys. Chem.  1964,  10:  95 
    Google Scholar
  • 12 Böeseken J. Recl. Trav. Chim. Pays-Bas  1922,  41:  722 
    Google Scholar
  • 13 von Orthner L. Freyss G. Justus Liebigs Ann. Chem.  1930,  484:  131 
    Google Scholar
  • 14 von Orthner L. Chem. Ber.  1928,  61:  116 
    Google Scholar
  • 15 Bonner TG. Bourne EJ. Saville NM. J. Chem. Soc.  1960,  2917 
    Google Scholar
  • 16 Schaeffer JR. Stevens RE. J. Org. Chem.  1973,  38:  1241 
    Google Scholar
  • 17 Perrin DD. Armarego WLF. Perrin DR. Purification of Laboratory Chemicals   Pergamon Press; London: 1980. 
    Google Scholar
  • 18 Vogel AI. Vogel"s Textbook of Practical Organic Chemistry   5th ed.:  Longman; London: 1989. 
    Google Scholar