64357-71-7

Upstream product

• 527-53-7 1,2,3,5-Tetramethylbenzene 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 618-32-6 Benzoyl bromide 
• 2142-78-1 1-(2,3,4,6-tetramethyl-phenyl)-ethanone 

Downstream Products

• 854247-35-1 1-phenyl-1-(2,3,4,6-tetramethyl-phenyl)-ethene 
• 527-53-7 1,2,3,5-Tetramethylbenzene 
• 65-85-0 benzoic acid 
• 2142-78-1 1-(2,3,4,6-tetramethyl-phenyl)-ethanone 
• 155785-79-8 1-acetyl-2-(nitrooxymethyl)-4,5,6-trimethylbenzene 
• 78740-45-1 1-acetyl-3-nitro-2,4,5,6-tetramethylbenzene 
• 103224-55-1 2-(nitromethyl)-4,5,6-trimethylacetophenone 
• 91390-77-1 1-propionyl-2,4,5,6-tetramethylbenzene 
• 69187-00-4 1,5-dipropionyl-2,3,4,6-tetramethylbenzene 
• 69313-51-5 1,3-diacetyl-2,4,5,6-tetramethylbenzene 

Relevant academic research and scientific papers

Graphite as an effective catalyst for Friedel-Crafts acylation

Graphite is found to promote Friedel-Crafts acylation of aromatic compounds such as anisole, toluene and o-xylene with acyl halides to give the corresponding acylated products in high yields.

Positional Reactivity of Acylpolymethylbenzenes in Electrophilic Substitution

Friedel-Crafts acylation, bromination, deuteration, and nitration of acetylpentamethylbenzene (APMB), 1-acetyl-2,3,4,6-tetramethylbenzene (ATMB), and 1-benzoyl-2,3,4,6-tetramethylbenzene (BTMB) and the resulting product distribution were investigated.Friedel-Crafts acylation, bromination, and deuteration of APMB and Friedel-Crafts acylation of ATMB gave deacetylation-substitution products.On the other hand, bromination and deuteration of ATMB (or BTMB) and Friedel-Crafts acylation of BTMB gave 5-substituted products.In both cases, the positional reactivities were in accordance with the relative ?-complex stability.Conversely, except for Friedel-Crafts-type nitration, the positional reactivities in the nitration of these substrates were strikingly different from those of the above three reactions.Thus, side-chain functionalization at the 6-methyl group occurred in nitration with fuming nitric acid, depending on the solvents in use.The NMDO calculations and the reaction of APMB with single-electron transfer reagents such as tetranitromethane-hν or cerium(IV) ammonium nitrate suggest that the product distribution in nitration can be explained in terms of a single-electron transfer mechanism.

2-(Trifluoromethylsulfonyloxy)pyridine as a Reagent for the Ketone Synthesis from Carboxylic Acids and Aromatic Hydrocarbons

A new reagent 2-(trifluoromethylsulfonyloxy)pyridine (TFOP) was prepared by the reaction of sodium salt of 2-pyridinol with trifluoromethylsulfonyl chloride in dioxane.The conpound TFOP in trifluoroacetic acid has been found to intermolecularly dehydrate from benzoic acid and aromatic hydrocarbons to give the corresponding benzophenones in high yield.It was further elucidated, in the reaction of fluorene, that a variety of carboxylic acids can be used as the acyl precursor for the aromatic ketone synthesis in conjunction with the TFOP/TFA system.This acylation procedure has been applied to the synthesis of 2-acylthiophenes, which are hard to prepare in a satisfactory yield by the classical Friedel-Crafts reaction using aluminum chloride as the catalyst.