(1) Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia
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%.