97125-18-3Relevant academic research and scientific papers
The Oxidation of 2,4,6-Trimethylphenol with Molecular Oxygen Catalyzed by a Copper(II)-Oxime or Copper(II)-Amine System
Shimizu, Masao,Watanabe, Yoshihito,Orita, Hideo,Hayakawa, Takashi,Takehira, Katsuomi
, p. 251 - 257 (2007/10/02)
2,4,6-Trimethylphenol (1a) was selectively oxidized to 3,5-dimethyl-4-hydroxybenzaldehyde (2a) by molecular oxygen in the presence of a copper(II) chloride-oxime or copper(II) chloride-amine catalyst in alcohol at ambient temperature.When an acid was present in the catalyst system, the formation of both 2,6-dimethyl-p-benzoquinone (3) and a formaldehyde dialkyl acetal was accelerated.It is likely that 2a is produced by way of the formation of a quinonemethide intermediate, followed by a repeated 1,6-addition of alcohol on the intermediate to form a 4-(alkoxymethyl)-2,6-dimethylphenol (5a), and then 3,5-dimethyl-4-hydroxybenzaldehyde dialkyl acetal, which would be hydrolyzed to 2a.When the reaction time was shortened, 5a was isolated in good yield.Oxidations of the other p-methyl-substituted phenols were also examined using the present oxidation system.
A Facile Synthesis of 4-Alkoxymethylphenols by a Copper(II)-Acetoxime Catalyst/O2 System
Shimizu, Masao,Watanabe, Yoshihito,Orita, Hideo,Hayakawa, Takashi,Takehira, Katsuomi
, p. 2053 - 2056 (2007/10/02)
4-Alkoxymethyl-2,6-dimethylphenols were synthesized from 2,4,6-trimethylphenol in good yields by a copper(II) chloride-acetoxime catalyst/molecular oxygen system in alcohols at ambient temperature.The oxidation of the other p-methylsubstituted phenols were also examined.
