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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 3
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Original Articles

Isomerization of Estragole to Anethole

Pages 225-231 | Published online: 05 Dec 2006

References

  • Wagner , A. P. 1952 . Manf. Chemist , 23 : 56 and references cited therein
  • In our hands a 56% converion of II to a 82:18 ratio of I:cis-isomer is obtained after 12 hr at 200°
  • Casey , C. P. and Cyr , C. R. 1973 . J. Am. Chem. Soc. , 95 : 2248 and references cited therein; J. E. Arnet and R. Pettit, Ibid, 83 2955(1961); P. W. Jolly, F. G. A. Stone and K. Mackenzie, J. Chem. Soc., 6416(1965); P. A. Spanninger and J. L. von Rosenbert, J. Org. Chem., 34, 3658(1969); M. A. Schroeder and M. S. Wrighton, J. Am. Chem. Soc., 98, 551(1976)
  • Tolman , C. A. 1972 . J. Am. Chem. Soc. , 94 : 2994 and references cited therein
  • Goldborn , P. and Schienmann , F. 1973 . J. Chem. Soc., Perkin I , : 2870
  • Corey , E. J. and Suggs , J. S. 1973 . J. Org. Chem. , 38 : 3224 M. Martan and P. H. Ruchenbacher, U. S. Patent. 4,038,325 (1977)
  • To assure that isomerization does not proceed at GLC injection port temperatures with catalyst residue, this ratio was corroborated by NMR in several experiments
  • Similar treatment of I affords an 95:4:1 ratio of I:cis-I:II
  • The active catalyst may be clustered; for simplicity a mononuclear species is presented
  • Use of anethole as a fragrance or flavor requires <1% contamination with the cis-isomer due to toxicity and sharp taste of the latter
  • Verley , A. German Patent 154,654 . 1902 .

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