81375-01-1

Upstream product

• 2929-45-5 (2-hydroxy-4,6-dimethylphenyl)(phenyl)methanone 
• 100923-72-6 4-amino-1-benzoyl-2,6-dimethylbenzene 
• 2050-45-5 N-acetyl-3,5-dimethylaniline 
• 95741-45-0 4-(benzyloxy)-2,6-dimethylbenzoic acid 
• 164654-82-4 4-Benzyloxy-2,6-dimethylbenzoylchlorid 
• 98-88-4 benzoyl chloride 
• 5554-28-9 (3,5-Dimethylphenyl)benzoat 
• 78589-19-2 4-acetamido-1-benzoyl-2,6-dimethylbenzene 

Downstream Products

• 2929-45-5 (2-hydroxy-4,6-dimethylphenyl)(phenyl)methanone 
• 5554-28-9 (3,5-Dimethylphenyl)benzoat 
• 108-68-9 3,5-Dimethylphenol 
• 78588-98-4 1-benzoyl-4-methoxy-2,6-dimethylbenzene 

Relevant academic research and scientific papers

The Fries Rearrangement as an Equilibrium Reaction

The Fries rearrangement of arylbenzoates 1, in 1,2-dichloroethane in the presence of trifluoromethanesulfonic acid (TFMS) as catalyst, to ortho- and para-hydroxyaryl ketones (2 and 3, resp.) is reversible at 170 deg C; an equilibrium of the compounds 1, 2, and 3 is established.The equilibrium is achieved starting from the aryl esters 1 as well as from the hydroxyaryl ketones 2 and 3, respectively.The higher stability of the ortho-compounds 2 compared to the para-compounds 3 can be explained by greater resonance interaction between the carbonyl group and the aromatic ring in 2.The torsion angles Θ, which are good indicators of this interaction, can be determined from 13C NMR spectra.A dissociative mechanism is proposed for the acryl group migration.