Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Convenient Procedure for the Reduction of Carboxylic Acids via Acyloxyborohydrides

  • Published : 1982.12.30
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Abstract

A new convenient method for the reduction of carboxylic acids to the corresponding alcohols via acyloxyborohydrides was explored. Acyloxyborohydrides, prepared from the reaction of various carboxylic acids and sodium borohydride, underwent reduction to the corresponding alcohols readily by the addition of dimethyl sulfate or Lewis acids, such as boron trifluoride etherate and triphenyl borate, presumably through acyloxyboranes. By utilizing this procedure, aliphatic and aromatic acids are rapidly and quantitatively reduced to the corresponding alcohols in terahydrofuran either at room temperature (or at $65^{\circ}$). This procedure provides selective reduction of carboxylic acids in the presence of halogen, nitro, and heterocyclic rings such as furan and thiophene.

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References

  1. Org. React. v.6 W. G. Brown
  2. J. Amer. Chem. Soc. v.88 H. C. Brown;P. M. Weissman;N. M. Yoon
  3. J. Amer. Chem. Soc. v.87 H. C. Brown;P. M. Weissmann
  4. J. Amer. Chem. Soc. v.88 H. C. Brown;N. M. Yoon
  5. Reduction with Complex Metal Hydrides N. G. Gaylord
  6. J. Org. Chem. v.38 N. M. Yoon;C. S. Pak;H. C. Brown;S. Krishnamurthy;T. P. Stocky
  7. J. Org. Chem. v.39 C. F. Lane;H. L. Myatt;J. Daniels;H. B. Hoppes
  8. J. Amer. Chem. Soc. v.99 H. C. Brown;T. P. Stocky
  9. J. Org. Chem. v.71 S. W. Chaikin;W. G. Brown
  10. J. Amer. Chem. Soc. v.82 H. C. Brown;Subba Rao
  11. J. Amer. Chem. Soc. v.82 T. Reetz
  12. Handbook of Chemistry and Physics(55th ed.) CRC. Press, Inc.
  13. Zh. Prikl. Khim. v.21 B. H. Bogosloskii;Z. S. Kazakova
  14. Chem Abstr. v.43 B. H. Bogosloskii;Z. S. Kazakova
  15. Yakugaku Zasshi v.96 A. Nose;T. Kudo
  16. J. Org. Chem. v.34 H. M. Bell;C. W. Vanderslices;A. Spehar
  17. J. Amer. Chem. Soc. v.90 H. C. Brown;R. L. Sharp
  18. Org. Reaction v.13 C. Zweifel;H. C. Brown
  19. J. Amer. Chem Soc. v.81 H. G. Weiss;I. Shapiro

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  1. Selective Reduction Among Carboxylic Acids with Sodium Borohydride vol.15, pp.10, 1985, https://doi.org/10.1080/00397918508063891