A New and Convenient Method for the Reduction of an Aromatic Carboxyl to a Methyl Group

Journal of the American Chemical Society

Volumn 92, Issue 10, 1970, Pages 3232-3233

  Benkeser, R A ^a   Foley, K M ^a   Gaul, J M ^a   Li, G S ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000824920     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00713a078     Document Type: Article

References (12)

1. V. Bazant, et al., Tetrahedron Lett., 3303 (1968).
2. H. S. Broadbent, G. C. Campbell, W. J. Bartley, and J. H. Johnson, J. Org. Chem., 24, 1847 (1959).
3. H. C. Brown and B. C. Subba Rao, J. Org. Chem., 22, 1135 (1957).
4. H. C. Brown and B. C. Subba Rao, J. Amer. Chem. Soc, 77, 3164 (1955).
5. R. F. Nystrom and W. G. Brown, J. Amer. Chem. Soc, 69, 2548 (1947).
6. S. Ono and T. Yamauchi, Bull. Chem. Soc, Jap., 25, 404 (1952).
7. H. A. Staab and H. Braunling, Justus Liebigs Ann. Chem., 654, 119 (1962).
8. Such a transformation can be achieved by reduction of the acid to the alcohol with lithium aluminum hydride and conversion of the alcohol to the tosylate, followed by a second reduction either with lithium aluminum hydride or Raney nickel and hydrogen. See N. G. Gaylord, “Reduction with Complex Met al Hydrides,” Interscience, New York, N. Y., 1956, p 855. Benzylic-type alcohols can also be reduced directly with hydrogen under pressure in the presence of various catalysts. See, for example
9. R. L. Shriner and R. Adams, J. Amer. Chem. Soc., 46, 1683 (1924). (b) Benzoic acid can be reduced to toluene with rhenium-type catalysts and hydrogen at high temperatures and pressures. See ref 2 and
10. H. S. Broadbent and D. W. Seegmiller, J. Org. Chem., 28, 2347 (1963).
11. R. A. Benkeser and J. M. Gaul, J. Amer. Chem. Soc, 92, 720 (1970).
12. C. Eaborn, “Organosilicon Compounds,” Butterworths, London, 1960, pp 143-146.