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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 20
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Original Articles

Catalytic Hydrogenation of L-Ascorbic Acid (Vitamin C): A Stereoselective Process for the Production of L-Gulono-1, 4-Lactone

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Pages 3263-3265 | Received 16 Mar 1995, Published online: 23 Sep 2006

References

  • Smith , M. B. 1994 . Organic Synthesis , 423 NY : McGraw-Hill .
  • Mackie , R. K. and Smith , D. M. 1983 . Guidebook to Organic Synthesis , 174 Essex, , England : Longman Group Limited .
  • Andrews , G. C. , Crawford , T. C. and Bacon , B. E. 1981 . J. Org. Chem. , 46 : 2976 – 2977 . We have found that complete reduction, with 10% palladium on carbon, proceeds in about 18 hours at ambient temperature. We evaluated the usual catalysts (Pt., Ru, Ni, etc.) and found minimal activity. CAUTION: in the case of activated Raney nickel (J. Org. Chem., Volume 26, 1961, page 1625) rapid decomposition of the ascorbic acid occurred, resulting in rapid pressure build-up leading to explosion of the Parr flask!
  • Dixon , M. and Webb , E. C. 1979 . Enzymes; , 3rd. Ed. , NY : Academic Press .
  • Hubschwerlen , C. 1986 . Synthesis , : 962 – 964 .
  • 1994–1995 . 744 Material has m.p. range identical to the L-gulono-1, 4-lactone of commerce. See: Aldrich Chemical catalog. (cat. #31,030–1)

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