Benzylic oxidation with palladium(II) acetate

✍ Scribed by David R. Bryant; James E. McKeon; Bernard C. Ream

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 149 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89496-4

✦ Synopsis

Sometime ago, we discovered that palladium(I1) acetate is an efficic'::t reagent for benzylic oxidation of alkylbenzenes.

For example, healing a mi_\ture of 0.10 mole of toluene, 0.20 mole of potassium acetate, and 0.01 mole of palladium(I1) acetate in 1.67 moles of acetic acid at 100' for 5 hours gave a 92.5% yield of benzyl acetate (based on palladium(I1) acetate), along with 6.0%

of benzylidene diacetate and a trace of benzaldehyde.

We were, therefore, somewhat surprised when van Helden and Verberg(1)

reported that the reaction of toluene with palladium(I1) chloride in acetic acid under strikingly similar conditions gave completely different results.