2929-45-5

Upstream product

• 65-85-0 benzoic acid 
• 108-68-9 3,5-Dimethylphenol 
• 5554-28-9 (3,5-Dimethylphenyl)benzoat 
• 81375-01-1 (4-Hydroxy-2,6-dimethylphenyl)phenylketon 
• 7446-70-0 aluminium trichloride 
• 201230-82-2 carbon monoxide 
• 24242-79-3 2-iodo-3,5-dimethyl-phenol 
• 98-80-6 phenylboronic acid 
• 501-65-5 diphenyl acetylene 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 611-71-2 MANDELIC ACID 
• 50341-26-9 4,6-dimethyl-3-phenylbenzofuran-2(3H)-one 
• 98-88-4 benzoyl chloride 
• 143815-10-5 benzoic acid-(2-bromo-4,5-dimethyl-phenyl ester) 

Downstream Products

• 855160-23-5 5,7-dimethyl-3,4-diphenyl-coumarin 
• 4072-20-2 1-benzoyl-2-methoxy-4,6-dimethylbenzene 
• 5554-28-9 (3,5-Dimethylphenyl)benzoat 
• 81375-01-1 (4-Hydroxy-2,6-dimethylphenyl)phenylketon 
• 108-68-9 3,5-Dimethylphenol 
• 4072-14-4 (4,5-dimethyl-2-hydroxyphenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones

We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.

Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage

A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.

Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: Application to the total synthesis of luteolin

A general and mild protocol for achieving the carbonylative cross-coupling of sterically hindered, ortho-disubstituted aryl ketones is reported. The commercially available PEPPSI-IPr catalyst is shown to efficiently promote the carbonylative cross-coupling of hindered ortho-disubstituted aryl iodides to give diaryl ketones; traditional phosphine catalysts are less effective. Carbonylative Suzuki-Miyaura cross-couplings provide a diverse array of biaryl ketones in good to excellent yields. The same catalyst is also shown to catalyze a carbonylative Negishi cross-coupling reaction, utilizing a variety of alkynyl-zinc reagents to give the corresponding alkynyl aryl ketones. Application of this new methodology to the synthesis of the natural product luteolin is reported.

Carbonylative cross-coupling of ortho-disubstituted aryl iodides. Convenient synthesis of sterically hindered aryl ketones

(Chemical Equation Presented) A mild and general protocol for the carbonylative cross-coupling of sterically hindered ortho-disubstituted aryl iodides is reported. Carbonylative Suzuki-Miyaura couplings of a variety of aryl boronic acids provide an array of substituted biaryl ketones in modest to excellent yield. A carbonylative Negishi coupling that utilizes alkynyl nucleophiles is also described.

Fries rearrangement in ionic melts

1-Butyl-3-methylimidazolium chloroaluminate, [BMIm]+Al2Cl7-, was used as a solvent as well as a Lewis acid catalyst in Fries rearrangement reactions of phenyl benzoates. The rate of consumption of phenyl benzoate obeyed first-order kinetics. Good yields and high selectivity are the features observed in this unconventional but interesting aprotic solvent.

Synthesis of vicinal 2,3-dialkyl-6-hydroxybenzophenones by titanium tetrachloride catalyzed Fries rearrangement of 3,4-dialkylphenyl benzoates

The titanium(IV) chloride-mediated Fries rearrangement of 3,4-dialkylphenyl benzoates 1 yields mainly 4,5-dialkyl-2-hydroxybenzophenones 2 in high yield. We describe here a new access to the unknown vicinal 2,3-dialkyl-6-hydroxybenzophenones 3, which is b

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.