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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 20
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Original Articles

A Practical Preparation of 4,4-Diphenylcyclohexanol: A Key Intermediate in the Synthesis of Ms-325

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Pages 3895-3906 | Received 22 Apr 1998, Published online: 23 Aug 2006

REFERENCES

  • McMurry , T. J. PCT Publication WO 96/23526
  • Diekman , H. W. , Buehring , K. U. , Garbe , A. and Nowak , H. 1976 . Arrzneim.-Forsch , 26 ( 4B ) : 722 – 6 . 4,4-Diphenylcyclohexanol has been found to be a metabolite of Pramiverine:
  • The only other report found to reference 4,4-Diphenylcyclohexanol . German Patent #1793611 . 1971 .
  • Cost analysis was completed from published information by Aldrich, Fluka and Sigma Chemical. The availability of 3,4 and 5 were investigated through Chemcyclopedia
  • Nomura , R. , Matsuno , T. and Endo , T. 1996 . J. Am. Chem. Soc. , 118 : 11666 – 11667 .
  • Fukuzawa , S. , Tsuchimoto , T. and Kanai , T. 1994 . Chemistry Lett , : 1981 – 1984 .
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  • Mukherjee , D. K. , Palit , B. K. and Saha , C. R. 1994 . J. Molecular Catalysis , 88 : 57 – 70 .
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  • No decrease in purity was observed after one year at -5.0–0.0°C
  • Zimmermann , H. , Keese , R. , Nasielski , J. and Swenton , J. S. 1966 . J. Am. Chem. Soc. , 88 : 4895 – 4904 .
  • From reference 13: It was not reported if the 95% ethanol was anhydrous
  • The remaining 5% is isopropanol
  • The cost of 99.0% MVK was twice that for the 94.0% material (Aldrich Chemical)
  • A complete reduction from 5 to 2 under hydrogenation conditions using 5% Pt-C/H2 at 30 psi has been recently achieved by Mallinckrodt Medical chemists (S. Woulfe et al), St. Louis, Mo. (Unpublished results)
  • Hydrogenation of 4,4-diphenylcyclohex-2-ene-1-one to 4,4-diphenylcyclohexanone has been reported
  • Bunce , R. A. , Taylor , V. L. and Holt , E. M. 1991 . J. Photochem. Photobiol. A: Chem. , 57 : 317 – 329 . The ketone was isolated and fully characterized
  • Frimer , A. A. 1989 . J. Org. Chem. , 54 : 4853 – 4866 .

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