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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 12-13
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Original Articles

Synthesis of Optically Active Cyanohydrins Using Almond Meal

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Pages 1387-1391 | Received 08 Apr 1991, Published online: 23 Sep 2006

References

  • Ziegler , T. , Hörsch , B. and Effenberger , F. 1990 . Synthesis , : 575
  • Brussee , J. , Roos , E. C. and Van der Gen , A. 1988 . Tetrahedron Lett. , 29 : 4485
  • Brussee , J. and Van der Gen , A. 1991 . Recl. Trav. Chim. Pays-Bas , 110 : 25
  • Brussee , J. , Dofferhoff , F. , Kruse , C. G. and Van der Gen , A. 1990 . Tetrahedron , 46 : 1653
  • Narasaka , K. , Yamada , T. and Minakawa , H. 1987 . Chem. Lett. , : 2073
  • Reetz , M. T. , Kunisch , F. and Heitmann , P. 1986 . Tetrahedron Lett. , 27 : 4721
  • Oku , J. and Inoue , S. 1981 . J. Chem. Soc. Chem. Comm. , : 229
  • Niedermeyer , U. and Kula , M.-R. 1990 . Angew. Chem. Int. Ed. Engl. , 29 : 386
  • Effenberger , F. , Ziegler , T. and Förster , S. 1987 . Angew. Chem. Int. Ed. Engl. , 26 : 458
  • Brussee , J. , Loos , W. T. , Kruse , C. G. and Van der Gen , A. 1990 . Tetrahedron , 46 : 979
  • Almond meal is commercially available from the Sigma Chemical Company. The material used in the experiments described here was prepared by grinding almonds and defatting three times with ethyl acetate
  • To avoid the use of free HCN and to saturate ethyl acetate with an acetate buffer pH = 5.5 the following procedure was followed: NaCN (2.1 g, 43 mmol) was dissolved in water (75 mL). Acetic acid was added until pH = 5.5. The HCN was then extracted with ethyl acetate (75 mL). The amount of HCN in the organic phase was determined by a slightly modified literature procedure14; 1.0 mL of the organic phase was diluted with 20 mL of water and 5 mL of a whirling Mg(OH)2 suspension in water and titrated with 0.1 N AgNO3 using K2CrO4 as indicator.
  • The cyanohydrins possess a similar spatial arrangement. Due to priority rules cyanohydrin 2c must be assigned the (S)-configuration
  • Horwitz , W. 1980 . “Official Methods of Analysis of the Association of Official Analytical Chemists”, , 13th ed. , 318 – 319 . Washington : AOAC .

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