Synthetic experiments in the benzopyrone series

Part XLIII. Preparation of 3-hydroxy flavanones
  • Om Parkash Goel
  • N. Narasimhachari
  • T. R. Seshadri


The action of iodine and silver acetate varies with the type of flavanones employed, and yields the intermediate stages postulated in the new flavone synthesis using iodine and sodium acetate. The polyhydroxyflavanones, naringenin and hesperetin form directly the 3-acetates which can be hydrolysed to the 3-hydroxy compounds. On the other hand from naringenin 7:4′-dimethyl ether and 5:7-dimethoxy flavanone, the 3-iodo compounds can be isolated as the first intermediates. The behaviour of the 3-hydroxy flavanones in acid and alkaline conditions also varies; either dehydrogenation to flavonol or dehydration to flavone taking place.

Our thanks are due to Dr. Pew of the Forest Products Laboratory, Madison, U.S.A., for the generous supply of 3-hydroxy naringenin used in this work.


Naringenin Dimethyl Ether Flavanone Hesperetin Galangin 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Oyamada..J. Chem. Soc. Japan, 1934,55, 755.Google Scholar
  2. 2.
    Kubota..Ibid., 1939,60, 604; 1938,59, 1053; 1938,59 1153.Google Scholar
  3. 3.
    Pew..J. Am. Chem. Soc., 1948,70, 3031.CrossRefGoogle Scholar
  4. 4.
    Kotake and Kubota..Ann., 1940,544, 253.Google Scholar
  5. 5.
    Zemplen and Bognar..Ber., 1943.76B, 452.Google Scholar
  6. 6.
    Kostanecki, Levi and Tambor..Ibid., 1899,32, 326.Google Scholar
  7. 7.
    Narasimhachari and Seshadri..Proc. Ind. Acad. Sci., 1949,30A, 151.Google Scholar
  8. 8.
    Seshadri..Biochem. Reviews, 1951,20, 498.Google Scholar
  9. 9.
    Kostaneccki and Tambor..Ber., 1904,37, 792.Google Scholar
  10. 10.
    Lindstedt..Acta Chem. Scand., 1950,4, 772.CrossRefGoogle Scholar
  11. 11.
    Kostanecki and Tambor..Ber., 1899,32, 2260.Google Scholar
  12. 12.
    Gupta, Narasimhachari and Seshadri..Jour. Sci. Ind. Res., 1953,12B, 229.Google Scholar
  13. 13.
    Pankajamani (Miss) and Seshadri..Proc. Ind. Acad. Sci., 1952,36A, 157.Google Scholar
  14. 14.
    Reichel and Steudel..Ann., 1942,553, 83.Google Scholar

Copyright information

© Indian Academy of Sciences 1954

Authors and Affiliations

  • Om Parkash Goel
    • 1
  • N. Narasimhachari
    • 1
  • T. R. Seshadri
    • 1
  1. 1.Department of ChemistryUniversity of DelhiDelhi

Personalised recommendations