Synthesis of 4-Hydroxycoumarion Derivatives-1: An Efficient Synthesis of Flocoumafen

  • Park, Oee-Sook (Department of Chemistry, Chungbuk National University) ;
  • Jang, Bong-Suek (Department of Chemistry, Chungbuk National University)
  • Published : 1995.08.01

Abstract

An anticoagulant, 4-hydroxy-3-[1, 2, 3, 4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyll-1 -naphthyl]coumarin (Flocoumafen) was synthesized in 8 steps starting from phenylacetyl shloride and anisole. The key step in the synthesis involves the reaction of 3-(4-methoxyphenyl)-1-teralol with 4-hydroxycoumarin to give 4-hydroxy-3 [1, 2, 3, 4-tetrahydro-3-[4-emthoxyphenyl]-1-naphthyl]coumarin.

Keywords

References

  1. J. Hyg. v.96 Field trials flocoumafen against war-farin-resistant infestations of the Norway rat (Rattus norvegicus Berk) Buckle,A.P.
  2. J. Org. Chem. v.36 Carbonium lon-Silane Hydride Tansfer Reaction. V. tert;Alkyl cations Carey,F.A.;Tremper,H.S.
  3. Austral. J. Chem. v.20 Flavan derivertives 16. Acid-catalyzed reactions of secondary benzyl alcohols and 1-tetralols in methanol Clark-Lewis,J.W.;Nair,V.
  4. Eur. Pat. Appl. EP 177,080 Process for preparing 4-hydroxy-coumarin derivatives Entwistle,J.D.;Boehm,P.
  5. J. Am. Chem. Soc. v.80 Five- vs. Six-membered Ring Formation in the Cyclization of 2.3.4-Triphenylbutyric Acid; the Relative Importance of Stereochemistry Lednicer,D.;Hauser,C.R.
  6. Bull. Chem. Soc. Japan. v.41 The stereo-chemistry of a tetralin-1-ols Mitsui,S.;Kasahara,A.;Hanaya,K.
  7. J. Hyg. v.96 The Susceptibility of Rattus rattus and Bandicota bengalensis to a new anticoagulant rodenticide, flocoumafen Parshad,V.R.;Chopra,G.
  8. International Biodeterioration v.24 Laboratory and Field Evaluation of Flocoumafen for Rodent control Parshad,V. R.
  9. Purification of laboratory chemicals (2nd ed.) Perrin,D.D.;Armarego,L.F.;Perrin,O.R.
  10. J. Hyg. v.95 Pen and field trials of a new anticoagulant rodenticide flocoumafen against the mouse (Mus musculus L.) Rowe,F.P.;Bradfield,A.;Swinney,T.
  11. J. Chem. Soc. Perkin. v.1 Synthesis of some Tetrahydronaphthyl-and-Flavanyl-coumarins Shadbolt,R.S.;Woodward,D.R.;Birchwood,P.J.
  12. Indian J. of Chem. v.26B Synthesis of 3-Aryl-1-tetralones Selvaraj,S.;Rajendran,A.S.;Arumugam,N.
  13. European Patent Separations of lsomers Whittle;Alan John