Synthesis 2009(4): 557-560  
DOI: 10.1055/s-0028-1083319
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Regioselective Preparation of 1,3-Dioxolane-4-methanol Derivatives from Glycerol Using Phosphomolybdic Acid

Nitin Wasantrao Fadnavis*, Reddipalli Gowrisankar, Gadupudi Ramakrishna, Mithilesh Kumar Mishra, Gurrala Sheelu
Biotransformations Laboratory, Discovery Block, Indian Institute of Chemical Technology, Uppal Road, Habsiguda, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: fadnavis@iict.res.in; e-Mail: fadnavisnw@yahoo.com;
Further Information

Publication History

Received 12 September 2008
Publication Date:
09 January 2009 (online)

Abstract

Phosphomolybdic acid (PMA) forms a blue-colored complex with glycerol in a 1:10 molar ratio. The glycerolato complex catalyzes conversion of glycerol into 1,3-dioxolane-4-meth­anol derivatives with complete regiospecificity in high yields (>95%) and the catalyst can be recycled up to ten times without loss of activity or regiospecificity.

    References

  • 1a Pagliaro M. Ciriminna R. Kimura H. Rossi M. Pina CD. Angew. Chem. Int. Ed.  2007,  46:  4434 
  • 1b Corma A. Iborra S. Velty A. Chem. Rev.  2007,  107:  2411 
  • 1c Armaroli N. Balzani V. Angew. Chem. Int. Ed.  2007,  46:  52 
  • 1d Chheda JN. Huber GW. Dumesic JA. Angew. Chem. Int. Ed.  2007,  46:  7164 
  • 2a Klepacova K. Mravec D. Kaszonyi A. Bajus M. Appl. Catal., A  2007,  328:  1 
  • 2b Ott L. Bicker M. Vogel H. Green Chem.  2006,  8:  214 
  • 2c Chai S.-H. Wang H.-P. Liang Y. Xu B.-Q. Green Chem.  2007,  9:  1130 
  • 3 Walsh RH. inventors; US  5268007. 
  • 4 Seemuth PD. inventors; US  4457763. 
  • 5 Jurczac J. Pikul S. Bauer T. Tetrahedron  1986,  42:  447 
  • 6 He DY. Li ZJ. Liu YQ. Qiu DX. Cai MS. Synth. Commun.  1992,  22:  2653 
  • 7a Kazumasa H, and Furukawa Y. inventors; US  6143908. 
  • 7b Kazumasa H, and Furukawa Y. inventors; US  6124479. 
  • 8a Kozhevnikow IV. Chem. Rev.  1998,  98:  171 
  • 8b Mizuno N. Misono M. Chem. Rev.  1998,  98:  199 
  • 8c Misono M. Ono K. Aoshima GA. Pure Appl. Chem.  2000,  72:  1305 
  • 9 Kitamura M. Isobe M. Ichikawa Y. Goto T. J. Am. Chem. Soc.  1984,  106:  3252 
  • 10a Izumi Y. Hasebe R. Urabe K. J. Catal.  1983,  84:  402 
  • 10b Yadav JS. Satyanarayana M. Balanarsaiah E. Raghavendra S. Tetrahedron Lett.  2006,  47:  6095 
  • 10c Nagaiah K. Sreenu D. Srinivasa Rao R. Vashishta G. Yadav JS. Tetrahedron Lett.  2006,  47:  4409 
  • 10d Abd El-Wahab MMM. Said AA. J Mol. Catal. A: Chem.  2005,  240:  109 
  • 10e Yadav JS. Raghavendra S. Satyanarayana M. Balanarsaiah E. Synlett  2005,  2461 
  • 11a Radoslovich EW. Raupach M. Slade PG. Taylor RM. Aust. J. Chem.  1970,  23:  1963 
  • 11b Taylor RM, and Brock AJ. inventors; US  4544761. 
  • 12 Tsigdinos GA. Hallada CJ. Inorg. Chem.  1968,  7:  437