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DOI: 10.1055/s-2003-42058
An Ionic Liquid Mediated Efficient Oxidation of Alcohols Using o-Iodoxybenzoic Acid (IBX) - a Simple and Eco-friendly Protocol
Publication History
Publication Date:
07 October 2003 (online)
Abstract
An environmentally benign ionic liquid is shown to be for the first time an excellent medium for mild and selective oxidation of alcohols using IBX at room temperature.
Key words
ionic liquid - hypervalent iodine reagents - selective oxidation - alcohols
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References
Representative Experimental Procedure of Compound 7: To 1 g of molten bmimCl was added 1 mmol of tetrahydro-1-naphthol and 1.2 mmol of IBX and the reaction mixture was stirred at r.t. TLC monitoring shows the completion of reaction in 15 min, after which 10 mL of water was added to the reaction mixture and extracted with EtOAc (3 × 15mL). The organic layer was separated, dried over anhyd Na2SO4, filtered and then evaporated under reduced pressure. The crude product thus obtained was purified by column chromatography (EtOAc/petroleum ether 1:9) to yield 0.133 g (91%) of tetralone.
111H NMR (500 MHz, CDCl3) data of N-Fmoc Valinal: δ = 9.64 (s, 1 H, CHO), 7.78-7.25 (m, 8 H), 5.47 (d, 1 H, J = 7.5 Hz, NH), 4.42-4.33 (m, 3 H, Fmoc-9-H, Fmoc-CH2), 4.23-4.21 (m, 1 H, 2-H), 2.29 (m, 1 H, 3-H), 1.03 [2 d, 6 H, CH(CH3)2, J CH3,3 = 6.9 Hz].