The remarkable role of water during the chemoselective reduction of ketones mediated by metallic aluminium

Tetrahedron Letters

Volumn 45, Issue 19, 2004, Pages 3775-3777

  Bhar, Sanjay ^a   Guha, Sharmistha ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

Aluminium and compounds; Reduction; Solvents and solvent effects

Indexed keywords

1 TETRALONE DERIVATIVE; ALKYL ARYL KETONE; ALUMINUM; CYCLOALKANONE; DIARYL KETONE; METAL; METHANOL; SODIUM HYDROXIDE; SOLVENT; WATER;

ARTICLE; POWDER; REDUCTION; STEREOCHEMISTRY;

EID: 1842861669     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.077     Document Type: Article

References (23)

1. Anastas P.T., Warner J.C. Green Chemistry-Theory and Practice. 1998;Oxford University Press.
2. Anastas P.T., Williamson T.C. Green Chemistry-Frontiers in Benign Syntheses and Processes. 1998;Oxford University Press.
3. Rajappa S. Emerging Eco-Friendly Alternatives for the Fine Chemical Industries. 2000;Sevak, Mumbai.
4. Li C.J., Chan T.-H. Organic Reactions in Aqueous Media. 1997;Wiley, New York.
5. Grieco P.A. Organic Synthesis in Water. 1997;Kluwer Academic, Dordrecht, The Netherlands.
6. Ribe S., Wipf P. Chem. Commun. 2001;299-307.
7. Dahlen A., Hilmersson G. Tetrahedron Lett. 43:2002;7197-7200.
8. Greeves, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 1-24.
9. Greeves, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 1-24.
10. (a) Yamamura, S.; Nishiyama, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 307-325;
11. (a) Yamamura, S.; Nishiyama, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 307-325;
12. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 8, pp 107-128;
13. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 8, pp 107-128;
14. (c) Mander, E. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 489-521.
15. (c) Mander, E. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 489-521.
16. Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 563-611.
17. Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. 1991; Vol. 3, pp 563-611.
18. Schreibmann A.A.P. Tetrahedron Lett. 1970;4271-4772.
19. Hulce M., LaVante T. Tetrahedron Lett. 29:1988;525-528.
20. Khurana J.M., Sehgal A., Gorgia A., Manian A., Maikap G.C. J. Chem. Soc., Perkin Trans. 1. 1996;2213-2215.
21. Hall S.S., Lipsky S.D., McEuroe F.J., Bartels A.P. J. Org. Chem. 36:1971;2588-2591.
22. Marcinow Z., Rabideau P.W. J. Org. Chem. 53:1988;2117-2119.
23. Typical experimental procedure: Aluminium powder (135 mg, 5 mmol) was added to a solution of benzophenone (182 mg, 1 mmol) in methanol (3 mL) followed by a solution of sodium hydroxide (100 mg, 2.5 mmol) in water (1.5 mL) with stirring. Stirring was continued until the completion of the reaction as monitored by TLC. The reaction mixture was diluted with water, dichloromethane was added and the mixture was filtered. The residue was repeatedly washed with dichloromethane and the aqueous layer was extracted twice with dichloromethane. The combined organic extracts were washed with water, dried and solvent was evaporated to furnish practically pure benzhydrol (156 mg, 85%).