Abstract
The solvent-free reduction of benzophenone and five substituted benzophenones with sodium borohydride to the corresponding alcohols was studied by thermal analysis, X-ray powder diffractometry, NMR spectroscopy, and scanning electron microscopy. In most cases, the reaction occurs via liquid eutectic phases that are formed between the benzophenone and the resulting benzohydrol. Nevertheless, this reaction can be carried out without the need for a solvent, leading to pure alcohol without side products. In some cases, heating may be necessary to achieve a reasonably short reaction time. In conclusion, this reaction type appears to be feasible as a preparative organic reaction that avoids a solvent.
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References
D. Seebach, Angew. Chem., 102 (1990) 1363.
J. M. Thomas, Pure Appl. Chem., 51 (1979) 1065.
L. Addadi, M. Cohen, M. Lahav and L. Leiserowitz, J. Chim. Phys. Phys. Chim. Biol., 83 (1986) 831.
Y. Ohashi (Ed.), Reactivity in molecular crystals, VCH, Weinheim 1993.
F. Toda, in Y. Ohashi (Ed.), Reactivity in molecular crystals, VCH, Weinheim 1993, p.177.
N. B. Singh and R.J. Singh, React. Solids, 8 (1990) 115.
B. S. Goud, K. Panneerselvam, D. E. Zacharias and G. R. Desiraju, J. Chem. Soc. Perkin Trans. 2, (1995) 325.
B. S. Goud and G. R. Desiraju, J. Chem. Res. S, (1995) 244.
M. Epple, S. Ebbinghaus, A. Reller, U. Gloistein and H. K. Cammenga, Thermochim. Acta, 269/270 (1995) 433.
F. Toda, K. Kiyoshige and M. Yagi, Angew. Chem., 101 (1989) 329.
G. W. H. Höhne, H. K. Cammenga, W. Eysel, E. Gmelin and W. Hemminger, Thermochim. Acta, 160 (1990) 1.
H. K. Cammenga, W. Eysel, E. Gmelin, W. Hemminger, G. W. H. Höhne and S. M. Sarge, Thermochim. Acta, 219 (1993) 333.
S. M. Sarge, E. Gmelin, G. W. H. Höhne, H. K. Cammenga, W. Hemminger and W. Eysel, Thermochim. Acta, 247 (1994) 129.
H. K. Cammenga and M. Epple, Angew. Chem. Int. Ed. Engl., 34 (1995) 1171.
N. B. Singh, R. J. Singh and N. P. Singh, Tetrahedron, 50 (1994) 6441.
R. Sato, T. Nagaoka, T. Goto and M. Saito, Bull. Chem. Soc. Jpn., 63 (1990) 290.
D. Giron, Thermochim. Acta, 248 (1995) 1.
T. L. Threlfall, Analyst, 120 (1995) 2435.
J. P. Dunitz and J. Bernstein, Acc. Chem. Res., 28 (1995) 193.
D.C. Wigfield, Tetrahedron, 35 (1979) 449.
W. E. Brown, D. Dollimore and A. K. Galwey (Eds.), Reactions in the solid state, Elsevier, Amsterdam 1980.
K. Bowden and M. Hardy, Tetrahedron, 22 (1966) 1169.
H. Schmalzried, Chemical Kinetics of Solids, VCH, Weinheim 1995.
H. Schmalzried, Ber. Bunsenges. Phys. Chem., 98 (1994) 1365.
M. Martin P. Tigelmann, S. Schimschaltholke and G. Schulz, Solid State Ionics, 75 (1995) 219.
J. Janek and C. Korte, Solid State Ionics, 85 (1996) 305.
M. Epple and L. Tröger, J. Chem. Soc., Dalton Trans., (1996) 11.
K. Schaum and K. Rosenberger, Z. anorg. Chem., 136 (1924) 329.
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Epple, M., Ebbinghaus, S. Reduction of Solid Benzophenones with Sodium Borohydride. Journal of Thermal Analysis and Calorimetry 52, 165–176 (1998). https://doi.org/10.1023/A:1010126626572
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DOI: https://doi.org/10.1023/A:1010126626572