5554-28-9

Upstream product

• 2929-45-5 (2-hydroxy-4,6-dimethylphenyl)(phenyl)methanone 
• 81375-01-1 (4-Hydroxy-2,6-dimethylphenyl)phenylketon 
• 65-85-0 benzoic acid 
• 108-68-9 3,5-Dimethylphenol 
• 287935-95-9 (3,5-dimethylphenyl)trimethoxysilane 
• 100-52-7 benzaldehyde 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 74542-54-4 N,N-phenyl-p-toluenesulfonylbenzamide 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 98-88-4 benzoyl chloride 

Downstream Products

• 2929-45-5 (2-hydroxy-4,6-dimethylphenyl)(phenyl)methanone 
• 4072-14-4 (4,5-dimethyl-2-hydroxyphenyl)(phenyl)methanone 
• 855160-23-5 5,7-dimethyl-3,4-diphenyl-coumarin 
• 347307-90-8 3,5-bis-[3,5-3,5-(dimethoxycarbonylphenoxymethyl)phenoxymethyl]phenyl benzoate 
• 347307-91-9 3,5-bis-[4-(methoxycarbonylphenoxymethyl)phenoxymethyl]phenyl benzoate 
• 347307-87-3 3,5-3,5-(dimethoxycarbonylphenoxymethyl)phenyl benzoate 
• 347307-88-4 3,5-4-(methoxycarbonylphenoxymethyl)phenyl benzoate 
• 347307-89-5 3,5-4-(methoxycarbonylphenoxymethyl)phenol 
• 186605-76-5 3,5-bis[3,5-bis(methoxycarbonyl)phenoxymethyl]phenol 
• 347307-84-0 3,5-bis(bromomethyl)phenyl benzoate 
• 81375-01-1 (4-Hydroxy-2,6-dimethylphenyl)phenylketon 
• 108-68-9 3,5-Dimethylphenol 

Relevant academic research and scientific papers

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Palladium-Catalyzed Aerobic Oxidative Coupling of Amides with Arylboronic Acids by Cooperative Catalysis

The first fluoride and palladium co-catalyzed conversion of amide to ester through an aerobic oxidative coupling pathway is reported. This new approach presents a practical process that employs easily available oxygen and commercially available arylboronic acids as coupling partners, uses a wide range of N- tosylamides, and proceeds under mild reaction conditions. This protocol demonstrates broad functional group tolerance, and provides an alternative option to synthesize esters from N-tosylamides which obtained by simply N-functionalization of secondary amides.

Transition-Metal-Free Poly(thiazolium) Iodide/1,8-Diazabicyclo[5.4.0]undec-7-ene/Phenazine-Catalyzed Esterification of Aldehydes with Alcohols

Poly(3,4-dimethyl-5-vinylthiazolium) iodide was used as a polymer precatalyst in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and phenazine for the oxidative esterification of aldehydes with alcohols. Selective functionalization of OH groups was achieved in the presence of NH2 groups. The poly(thiazolium) iodide/DBU/phenazine system exhibited excellent catalytic activity and could be reused five times without loss of activity.

Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids to access phenolic esters

A Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids with arylboronic acids is described. It represents a facile and practical methodology to access phenolic esters in moderate to good yields. The procedure tolerates a series of functional groups, such as methoxycarbonyl, acetoxy, free phenolic hydroxyl, vinyl, nitro, trifluoromethyl, methoxyl, bromo, chloro, iodo, and acetyl groups.

Copper(II)-catalyzed esterification of arenecarboxylic acids with aryl- and vinyl-substituted trimethoxysilanes

In this paper, the copper(II)-catalyzed esterification reaction of arenecarboxylic acids with aryl- or vinyl-substituted trimethoxysilanes is described. A series of aryltrimethoxysilanes and arenecarboxylic acids worked well under this procedure, affording aryl benzoate derivatives in moderate to good yields. Notably, trimethoxy(vinyl)silanes also worked well under this procedure giving a facile and versatile method to access vinyl benzoate derivatives. Georg Thieme Verlag Stuttgart.

Process for producing esterificated condensate

The present invention provides a method for preparing ester or thioester that can conduct catalytic esterification reaction with an equimolar amount of carboxylic acid and alcohol, or catalytic thioesterification reaction with carboxylic acid and an equimolar amount or small amount of thiol, and can be expected as an industrial method that needs an enormous amount of synthesis in the light of green chemistry. By using hafnium chloride (IV), especially tetravalent hafnium compounds represented by hafnium chloride (IV)?(THF)2 or hafnium (IV)t-butoxide as a (poly) condensation catalyst, direct condensation reaction is conducted from carboxylic acid and an equimolar amount of alcohol or a little smaller amount of thiol, in the nonpolar solvent such as toluene and the like, in a deoxidization atmosphere and under heating reflux, and the reaction synthesizes ester monomer or thioester monomer, polyester or polythioester. When heating reflux is conducted by using a nonpolar solvent, it is preferable to remove azeotropic water from the reaction system.

Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts

To promote atom efficiency in synthesis and to avoid the generation of environmental waste, the use of stoichiometric amounts of condensing reagents or excess substrates should be avoided. In esterification, excess amounts of either carboxylic acids or alcohols are normally needed. We found that the direct condensation of equimolar amounts of carboxylic acids and alcohols could be achieved using hafnium(IV) or zirconium(IV) salts. These metal salts are highly effective as catalysts for the selective esterification of primary alcohols with carboxylic acids in the presence of secondary alcohols or aromatic alcohols. The present methods can be applied to direct polyesterification and may be suitable for large-scale operations.

New simple convergent synthetic method for benzyl aryl ether dendritic structures

Phenolic benzyl aryl ether based dendrons with an ester periphery are easily prepared by convergent strategy through hydroxy substituted methyl benzoates and easily attainable benzoyl protected 3,5-bis(bromomethyl)phenol. The dendrons obtained can afford dendronized styrenes.

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.