USE OF ALUMINA IN PREPARATION OF OXIME: A PRECURSOR FOR BECKMANN REARRANGEMENT
Objective: Oxime is an important precursor for many reactions like Beckmann rearrangement, oxime ether preparation etc. Oxime is generally prepared in strong acidic , strong basic  medium. Even some methods involving mild basic medium  is also known. But these procedures involve hazardous chemicals like inorganic acid, inorganic base, organic bases like Pyridine , Hyamine  etc. Some green methodologies have been also developed but that also involve expensive reagents like Bi2O3  etc. Inthis context this work has been carried out to develop a new methodology for oxime preparation.
Methods: Different oxims have been prepared in heating condition using water-ethanol medium and alumina as a base. Products have been isolated by column chromatography using 200 mesh silica gel followed by fractional crystallization. Products were verified by melting point analysis.
Results: Four different aromatic oxims have been prepared in excellent yield and in an economically viable condition.
Conclusion: Here preparation of oxime in a mild basic medium has been reported. Alumina (Al2O3) is pretty cheap and not mentionable hazardous and it has been used here for the first time in synthesis of oxime.Keywords: Alumina, Beckmann Rearrangement, Column Chromatography, Ethanol, Hydroxylamine Hydrochloride, Oxime, Thin Layer Chromatography.
Weissermer K, Arpe HJ. Performance of immersion-type quartz steel-pouring nozzles with lateral delivery of the molten metal. Industrial Organic Chem 1978;19(3-4):222-5.
DamljanoviÄ‡ I, VukiÄ‡eviÄ‡ M, VukiÄ‡eviÄ‡ RD. Monatshefte fur Chemie 2006;137:301-305.
Sharghi H, Hosseini M. Synthesis 2002;1057-1059.
Rahman MM, Halim ME, Ahmed SM, Akhter K, Romman UKR, Ahmed MG. Bangladesh J. Sci. Ind. Res. 2013;48:7-12.
Lad UP, Kulkarni MA, Patil RS. Rasayan J. Chem. 2010;3:425-428
Saikia L, Baruah JM, Thakur AJ. Organic and Medicinal Chemistry Letters 2011;1:12.
Beckmann, E. Ber. Dtsch. Chem. Ges 1886;19:988-993.
Aghapour G, Amirabadi M. Indian J. Chem. 2007;46B: 649-652.
Chiang YH. J Org Chem. 1971;36:2146.
Smith PA, Robertson JE. J. Am. Chem. Soc. 1962;84:1197.
Dave PR, Forshar F. J. Org. Chem. 1996;61:8897-8903.
Shinada T, Yoshihara K. Tetrahedron Lett. 1995;37:6701-6704.
Ley JP, Bertram HJ. Bioorgan Med. Chem. 2001;9:1879-1885.