PDF herunterladen
Synlett 2004(9): 1575-1576  
DOI: 10.1055/s-2004-829535
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aromatic Aldehydes by Oxidative Hydroxymethylation

Olena Branytska, Ronny Neumann*
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Fax: +972(8)9344142; e-Mail: Ronny.Neumann@weizmann.ac.il;
Weitere Informationen

Publikationsverlauf

Received 1 April 2004
Publikationsdatum:
29. Juni 2004 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A new high yield method for the synthesis of aromatic ­aldehydes has been developed. The procedure is based on an acid catalyzed hydroxymethylation of an arene substrate by paraformaldehyde with concurrent selective oxidation of the intermediate aromatic carbinol by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to the aldehyde product.

Key words

aldehydes - arenes - electrophilic aromatic substitutions - oxidations - quinones

    References

  • 1 Haines AH. Methods for the Oxidation of Organic Compounds   Academic Press; London: 1988. 
    Google Scholar
  • 2 Rylander PN. Catalytic Hydrogenation in Organic Syntheses   Academic Press; New York: 1979. 
    Google Scholar
  • 3 Heck RF. Palladium Reagents in Organic Syntheses   Academic Press; London: 1985. 
    Google Scholar
  • 4 Crounse NN. Org. React.  1949,  5:  290 
    Google Scholar
  • 5 Truce WE. Org. React.  1957,  9:  37 
    Google Scholar
  • 6 Jutz C. Adv. Org. Chem.  1976,  9:  225 
    Google Scholar
  • 7 Wynberg H. Meijer EW. Org. React.  1982,  28:  1 
    Google Scholar
  • 8 Reiche A. Gross H. Höft E. Chem. Ber.  1960,  93:  88 
    CrossrefGoogle Scholar
  • 9 Olah GA. Kuhn SJ. J. Am. Chem. Soc.  1960,  82:  2380 
    CrossrefGoogle Scholar
  • 10a Casnati G, Casiraghi G, Puglia G, Sartori G, and Terenghi G. inventors; US Patent  4,151,201. 
    Crossref
  • 10b Casiraghi G. Casnati G. Puglia G. Sartori MG. Terenghi G. J. Chem. Soc., Perkin Trans. 1  1980,  1862 
    CrossrefGoogle Scholar
  • 10c Furukawa Y, and Keishi K. inventors; US Patent  6,080,895. 
    Crossref
  • 11 Matsuda T, and Murata T. inventors; US Patent  4,231,967. 
  • 12 Lee RJ, and Baranowski LJ. inventors; US Patent  4,371,712. 
  • 13 Virnig MJ. inventors; US Patent  4,638,096. 
  • 14 Bigi F. Conforti ML. Maggi R. Sartori G. Tetrahedron  2000,  56:  2709 
    CrossrefGoogle Scholar
  • 15 Jyothi TM. Talawar MB. Rao BS. Catal. Lett.  2000,  64:  151 
    CrossrefGoogle Scholar
  • 16a Becker HD. Bjoerk A. Adler E. J. Org. Chem.  1980,  45:  1596 
    Google Scholar
  • 16b Khenkin AM. Vigdergauz I. Neumann R. Chem.-Eur. J.  2000,  6:  875 ; and references therein
    Google Scholar
  • 17a Newman MS. Khanna VK. Org. Prep. Proced. Int.  1985,  17:  422 
    Google Scholar
  • 17b Kim KH. Grunewald GL. Org. Prep. Proced. Int.  1976,  8:  141 
    Google Scholar