Oxidation of Benzyl Ethers in Sodium Hypochlorite Mediated Piperidine-1-oxyl System

촉매량의 Piperidine-1-oxyl과 NaOCl계에서 벤질 에테르 유도체들의 산화 반응

  • Cho, Nam Sook (Department of Chemistry, Chungnam National University) ;
  • Park, Chan Heun (Department of Chemistry, Chungnam National University)
  • Published : 19950800

Abstract

The oxidation of various benzyl ethers and benzyl alkyl ethers to benzoates has been studied in two-phase system of $CH_3CO_2Et$ and aqueous NaOCl (6.6 mol eq.). The oxidant N-oxo-4-methoxy-2,2,6,6-tetramethylpiperidium bromide (N-oxoammonium salt) was prepared in situ and recycled by addition of 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl (0.03 mol eq., 4-methoxy-TEMPO), co-catalyst KBr (0.03mol eq.) and second oxidant NaOCl. Thus the catalytic amount of 4-methoxy-TEMPO was used. An adjustment of the pH value of below 8.0 was also required for this reaction with 2.5 hr of reaction time at 0∼5$^{\circ}C$. Under these conditions benzyl ethers were oxidized to benzoates. The selectivity of oxidation of benzyl alkyl ethers is dependent on the acidity of hydrogen and steric effect of alkyl group.

Keywords

References

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