Acetoxymethylation of benzene, toluene and related compounds with TeO2/HOAc

✍ Scribed by Jan Bergman; Lars Engman

• Book ID: 104237303
• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 154 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)85616-1

✦ Synopsis

Catalytic systems containing Te02 and HOAc have attracted considerable attention 192 in recent years. Ethylene, for example, can be catalytically converted to ethylene glycol in high yields (95%): C2H4 + l/2 O2 + 2 HOAc Te02 HB~AcOCH~CH~OAC + H20 AcOCH2CH20Ac + 2 H20 -HOCH2CH20H + 2 HOAc 'C2H4 + 112 O2 + H20 -HOCH2CH20H Recently a group at Phillips Petroleum reported3 that alkyl-substituted aromatic compounds, not unexpectedly4 , could be catalytically oxidized by a similar procedure. Thus toluene in one example (150 'C, 02, 50 psig initially at 24 'C, HOAc, Te02, gave benzyl acetate (76% yield) together with small amounts of benzaldehyde derivatives (8%) as well as other minor products In this paper we report different results tion of pressured 02). LiBr, LiN03) (7X), bromo-(partly unspecified). using similar systems (without introduc-120°,HOAc Te02,LiBr Ch2OAc Relative yields5: ortho 50X, meta 12X, para 38% * Part 2 in the series "Tellurium in Organic Synthesis". For part 1 see ref. 15.