53574-78-0

Upstream product

• 93-56-1 phenylethane 1,2-diol 
• 3277-27-8 diethyl benzoylphosphonate 
• 98-88-4 benzoyl chloride 
• 96-09-3 styrene oxide 
• 65-85-0 benzoic acid 
• 75-77-4 chloro-trimethyl-silane 
• 618-32-6 Benzoyl bromide 
• 61235-70-9 (+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan 
• 532-32-1 sodium benzoate 
• 93-97-0 benzoic acid anhydride 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 4141-38-2 2,4-diphenyl-1,3-dioxolane 

Downstream Products

• 10335-95-2 2-hydroxy-2-phenylethyl benzoate 

Relevant academic research and scientific papers

A polylinear regression model taking into account the cross effects of the structure and temperature in the reactions of phenyloxirane with benzoic acids, catalyzed by pyridines: Evidence of the isoparametricity phenomenon

The joint effect of the structure and temperature on the rate of the reactions of phenyloxirane with Y-substituted benzoic acids in acetonitrile, catalyzed by X-substituted pyridines, was studied. A polylinear regression model that adequately describes the effects of cross-varied factors was calculated. Owing to intensive interaction of the effects of the substituents X and temperature, experimental evidence for the isoparametricity phenomenon was obtained. Pleiades Publishing, Ltd., 2013.

Isoparametricity phenomenon and kinetic enthalpy-entropy compensation effect: Experimental evidence obtained by investigating pyridine-catalyzed reactions of phenyloxirane with benzoic acids

The joint effect of structure and temperature on the rate and free activation energy of reactions between phenyloxirane and substituted benzoic acids catalyzed by substituted pyridines in acetonitrile has been investigated. A correlation analysis of the results of a multifactor kinetic experiment indicates the additivity of the joint effects of structural factors (substituents X in pyridines and substituents Y in benzoic acids) and of the effects of the substituents Y and temperature. Intensive interaction (nonadditivity) is observed between the effects of the substituents X and temperature. This fact has provided experimental evidence for the existence of the enthalpy-entropy compensation aspect of the isoparametricity phenomenon: at the isoparametric temperature point (isokinetic temperature), the rate (free activation energy) of the process is independent of the structure of the substituent X because of the existence of an enthalpy-entropy compensation effect; on passing through this point, an inversion of the effect of X on the catalytic activity of pyridines takes place (isoparametricity paradox). At the isoparametric point with respect to the substituent X constant, there is no temperature effect on the reaction rate because of the activation enthalpy being close to zero. The isoparametric properties of a cross series of reactions are used to describe the mechanism of the pyridine-catalyzed opening of the oxirane ring.

Size-Induced Inversion of Selectivity in the Acylation of 1,2-Diols

Relative rates for the Lewis base-catalyzed acylation of aryl-substituted 1,2-diols with anhydrides differing in size have been determined by turnover-limited competition experiments and absolute kinetics measurements. Depending on the structure of the anhydride reagent, the secondary hydroxyl group of the 1,2-diol reacts faster than the primary one. This preference towards the secondary hydroxyl group is boosted in the second acylation step from the monoesters to the diester through size and additional steric effects. In absolute terms the first acylation step is found to be up to 35 times faster than the second one for the primary alcohols due to neighboring group effects.

The Activation of Carboxylic Acids via Self-Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation

The heterodimerizing self-assembly between a phosphoric acid catalyst and a carboxylic acid has recently been established as a new activation mode in Br?nsted acid catalysis. In this article, we present a comprehensive mechanistic investigation on this activation principle, which eventually led to its elucidation. Detailed studies are reported, including computational investigations on the supramolecular heterodimer, kinetic studies on the catalytic cycle, and a thorough analysis of transition states by DFT calculations for the rationalization of the catalyst structure-selectivity relationship. On the basis of these investigations, we developed a kinetic resolution of racemic epoxides, which proceeds with high selectivity (up to s = 93), giving the unreacted epoxides and the corresponding protected 1,2-diols in high enantiopurity. Moreover, this approach could be advanced to an unprecedented stereodivergent resolution of racemic α-chiral carboxylic acids, thus providing access to a variety of enantiopure nonsteroidal anti-inflammatory drugs and to α-amino acid derivatives.

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.

Efficient Ring opening reaction of epoxides with oxygen nucleophiles catalyzed by quaternary onium salt

Ring opening reactions of epoxides with oxygen nucleophiles catalyzed by a variety of quaternary onium salt, such as ammonium or phosphonium salt were explored. The results showed that tetrabutylphosphonium bromide (TBPB) among salts serves as the most ef

N-acyl 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) tetraphenylborate salts as O-acylating agents

Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been shown to be effective O-acylating agents, reacting with both primary and secondary alcohols to give the corresponding esters in good yields. In the case of diols, the N-acyl DBN·BPh4 salts have been shown to acylate regioselectively the primary alcohol functionality in the presence of a secondary alcohol. The DBN hydrotetraphenylborate side product can be readily removed by filtration, providing the ester products without the need for further purification.

Studies on DMDO-mediated benzylidene acetal oxidation

We have shown that dimethyldioxirane (DMDO) can be used to effect an oxidative partial deprotection of benzylidene acetals derived from both 1,2- and 1,3-diols to afford hydroxy benzoate products. A wide range of functional groups are tolerated, and good to excellent yields are usually observed. The reactions are easy to perform and produce little waste other than acetone.

An Efficient Method for the Chemoselective Preparation of Benzoylated 1,2-Diols from Epoxides

A very efficient and highly regioselective ring-opening reaction of epoxides with benzoic acid and its derivatives in the presence of cat. amount of tetrabutylammonium bromide (TBAB) in anhydrous acetonitrile has been developed. This effective method is useful for the preparation of selectively protected diols as precursor for many organic syntheses such as those of acyclic nucleosides and other synthetic purposes. The advantages of this method are efficiency, selectivity, low cost, and the applicability in large-scale synthesis of β-benzoyloxyalkanols.

Ring opening of epoxides with carboxylates and phenoxides in micellar media catalyzed with Ce(OTf)4

Efficient ring opening reaction of epoxides with carboxylates and phenoxide anions catalyzed with ceric triflate is performed in micellar media. This new method is a useful procedure for the preparation of β-carboxy and phenoxy alcohols from epoxides under mild reaction conditions.