Indirect electrooxidation (an ex-cell method) of alkylbenzenes by recycle use of (NH4)2Ce(NO3)6 in various solvent systems

Sigeru Torii, Hideo Tanaka, Tsutomu Inokuchi, Shoji Nakane, Mitsuo Akada, Norio Saito, Tosifumi Sirakawa

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Abstract

Indirect electrooxidation (an ex-cell method) of the side chain of alkylbenzenes has been performed by recycle use of (NH4)2Ce(NO3)6 (CAN) in various solvent systems. The side-chain oxidation of p-methoxytoluene (1) with CAN in methanol proceeds smoothly, yielding anisaldehyde (3, 94%), while use of aqueous methanol or acetic acid resulted in a mixture of 3 and the dimeric product 4 (19-35%) along with complex products (28-47%). Electrooxidation of the recovered cerium(III) salts was performed smoothly in methanol by passing 1.1-1.2 F/mol of electricity to give a reddish methanol solution of CAN, which can be used for the next oxidation of 1. The repeated use of CAN over 10 times produced the desired 3 in over 90% yields. Similarly, the oxidation of alkylbenzenes, bearing a p-methoxy group, gave the corresponding side-chain-oxidized products. In contrast, p-tert-butyltoluene (9e) could be oxidized by heating with CAN in aqueous 50% acetic acid at 85-90°C to give p-tert-butylbenzaldehyde in over 90% yield. The regeneration of CAN after the oxidation of 9e was also accomplished by electrolysis in the aqueous 50% acetic acid system. The reaction mechanisms in connection with the nature of CAN in various solvent systems are discussed.

Original languageEnglish
Pages (from-to)1647-1652
Number of pages6
JournalJournal of Organic Chemistry
Volume47
Issue number9
Publication statusPublished - 1982

ASJC Scopus subject areas

  • Organic Chemistry

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    Torii, S., Tanaka, H., Inokuchi, T., Nakane, S., Akada, M., Saito, N., & Sirakawa, T. (1982). Indirect electrooxidation (an ex-cell method) of alkylbenzenes by recycle use of (NH4)2Ce(NO3)6 in various solvent systems. Journal of Organic Chemistry, 47(9), 1647-1652.