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Selective Oxidation of Acetophenones Bearing Various Functional Groups to Benzoic Acid Derivatives with Molecular Oxygen
Author(s) -
Nakamura Ryota,
Obora Yasushi,
Ishii Yasutaka
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900099
Subject(s) - chemistry , terephthalic acid , benzoic acid , catalysis , halogen , alkoxy group , alkyl , manganese , cobalt , medicinal chemistry , oxygen , molecular oxygen , organic chemistry , polyester
Acetophenones substituted by alkyl, alkoxy, acetoxy, and halogen groups were selectively oxidized with molecular oxygen to the corresponding benzoic acids by using the N , N′ , N′′ ‐trihydroxyisocyanuric acid (THICA)/cobalt(II) acetate [Co(OAc) 2 ] and THICA/Co(OAc) 2 /manganese(II) acetate [Mn(OAc) 2 ]. For example, 4‐methylacetophenone was selectively oxidized with molecular oxygen to 4‐acetylbenzoic acid (85%) by THICA/Co(OAc) 2 and to 4‐methylbenzoic acid (93%) by Mn(OAc) 2 , while terephthalic acid was obtained in 93% with the THICA/Co(OAc) 2 /Mn(OAc) 2 catalytic system. It is interesting that the acetyl group on the aromatic ring is efficiently converted by a very small amount of Mn(OAc) 2 to the corresponding carboxylic acid, and that the present method provides a versatile route to acetylbenzoic acids which are difficult to prepare by conventional methods.