Abstract
Electroreduction of alkylphenones Ph-CO-(CH2)2R, where R = CH3-, C2H5-, C4H9-, allows the corresponding diols of the general composition [R(CH2)2-PhC(OH)-PhC(OH)-(CH2)2R] to be synthesized. This process was carried out in 0.2 M Et4NBr solution in dimethylformamide under the conditions of diaphragmless galvanostatic electrolysis with a Pt cathode and a Mg (Zn) anode at a current of 0.2 A and a temperature of 30°C. Optimization of this process makes it possible to synthesize a mixture of meso/dl isomers of target products (the meso/dl ratio depends on the R size and varies from 1/0.30 to 1/0.08) with the overall yields of 31–62% per the loaded ketone for its conversion by 52–86%.
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Rubtsov, M.V. and Baichikov, A.G., in Sinteticheskie khimiko-farmatsevticheskie preparaty (Synthetic Chemical Pharmaceutical Drugs) Moscow: Meditsina, 1971, pp. 82, 103.
Lyalin, B.V., Kashparov, K.I., and Petrosyan, V.A., Elektrokhimiya, 2006, vol. 42, p. 890.
Tanaka, N. and Kasai T., Bull. Chem. Soc. Jpn, 1981, vol. 54, p. 3026.
Mosher, W.A. and Heindel, N.D., J. Org. Chem., 1963, vol. 28, p. 2154.
Clerici A. and Porta O., J. Org. Chem., 1985, vol. 50, p. 76.
Ogawa, A., Takeuchi, H., and Hirao, T., Tetrahedron Lett., 1999, vol. 40, p. 7113.
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Original Russian Text © B.V. Lyalin, K.I. Kashparov, V.A. Petrosyan, 2008, published in Elektrokhimiya, 2008, Vol. 44, No. 12, pp. 1493–1497.
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Lyalin, B.V., Kashparov, K.I. & Petrosyan, V.A. Electroreduction of alkylphenones in diaphragmless cell with soluble anode. Russ J Electrochem 44, 1393–1396 (2008). https://doi.org/10.1134/S1023193508120136
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DOI: https://doi.org/10.1134/S1023193508120136