22618-23-1Relevant articles and documents
Synthesis and characterization of (E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol from 2-hydroxy-4,5-dimethylacetophenone
Deshmukh, Ajay,Dwivedi, Poonam,Gagare, Dinkar,Lokhande, Rama,Patil, Raju
, (2020)
This study reports the development of a novel substituted hydrazone prepared from 2-hydroxy-4,5-dimethylacetophenone and hydrazine in alkaline medium at controlled conditions which yields as corresponding hydrazone [(E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol]. The structure of synthesized (E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol was elucidated by elemental analysis and spectroscopic techniques like infrared spectroscopy, ultraviolet–visible spectroscopy, high-performance liquid chromatography, proton nuclear magnetic resonance and mass spectrum.
An efficient method to prepare aryl acetates by the carbonylation of aryl methyl ethers or phenols
Zhang, Dejin,Yang, Guoqiang,Xiong, Junping,Liu, Jia,Hu, Xingbang,Zhang, Zhibing
, p. 2683 - 2687 (2021/02/16)
Synthesis of valuable chemicals from lignin based compounds is critical for the application of biomass. Here, we develop a method of preparing aryl acetates by the carbonylation of aryl methyl ethers or phenols under low CO pressure. Good to excellent yields of aryl acetates were obtained using different substrates, and a possible reaction mechanism was proposed by conducting a series of control experiments. This method may provide a potential way for the utilization of lignin.
Substrate substitution effects in the Fries rearrangement of aryl esters over zeolite catalysts
Bonrath, Werner,Létinois, Ulla,Lin, Ronghe,Medlock, Jonathan,Mitchell, Sharon,Netscher, Thomas,Pérez-Ramírez, Javier,Stemmler, René T.
, p. 4282 - 4292 (2020/07/30)
The catalytic transformation of aryl esters to hydroxyacetophenones via Fries rearrangement over solid acids is of interest to avoid the use of corrosive and toxic Lewis and Br?nsted acids traditionally applied. Microporous zeolites are known to catalyze the reaction of simple substrates such as phenyl acetate, but their application to substituted derivatives has received limited attention. To refine structure-activity relationships, here we examine the impact of various parameters including the solvent polarity, water content, acidic properties, and framework type on the reaction scheme in the Fries rearrangement of p-tolyl acetate over common solid acids. The results confirm the importance of providing a high concentration of accessible Br?nsted acid sites, with beta zeolites exhibiting the best performance. Extension of the substrate scope by substituting methyl groups in multiple positions identifies a framework-dependent effect on the rearrangement chemistry and highlights the potential for the transformation of dimethylphenyl acetates. Kinetic studies show that the major competitive path of cleavage of the ester C-O bond usually occurs in parallel to the Fries rearrangement. The possibility of sequentially acylating the resulting phenol depends on the substrate and reaction conditions.