4118-51-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-2-phenylacetic acid isopropyl ester is used as an impurity reference substance for the synthesis and quality control of Pregabalin (P704800), a widely prescribed medication for various neurological conditions such as epilepsy, neuropathic pain, and generalized anxiety disorder. Its presence as an impurity in the final product is crucial for ensuring the safety, efficacy, and quality of Pregabalin.
Used in Material Science:
In the field of material science, 2-Hydroxy-2-phenylacetic acid isopropyl ester is utilized in the development of nonporous silica/alumina amorphous materials. These materials have potential applications in catalysis, adsorption, and other industrial processes due to their unique structural and chemical properties. The incorporation of Isopropyl DL-Mandelate can enhance the performance of these materials by modifying their surface properties and reactivity.

InChI:InChI=1/C11H14O3/c1-8(2)14-11(13)10(12)9-6-4-3-5-7-9/h3-8,10,12H,1-2H3

Upstream product

• 611-71-2 MANDELIC ACID 
• 67-63-0 isopropyl alcohol 
• 1074-12-0 phenylglyoxal hydrate 
• 14758-41-9 2-Hydroxy-2-phenyl-1,1,1-tris-(phenylmercapto)-aethan 
• 31197-66-7 isopropyl benzoylformate 
• 4861-85-2 isopropyl phenylacetate 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 264882-04-4 2-diazo-2-phenylacetic acid isopropyl ester 
• 104-54-1 3-Phenylpropenol 
• 25726-04-9 phenylglyoxylyl chloride 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 611-73-4 Benzoylformic acid 
• 934-56-5 trimethyl(phenyl)stannane 

Downstream Products

• 6818-08-2 iso-propyl (+/-)-O-acetylmandelate 
• 31197-66-7 isopropyl benzoylformate 
• 89015-27-0 (R)-α-hydroxyphenylacetic acid iso-propyl ester 
• 53439-96-6 (S)-α-hydroxyphenylacetic acid iso-propyl ester 
• 53697-63-5 (+/-)-bromo-phenyl-acetic acid isopropyl ester 
• 921754-35-0 isopropyl fluorophenylacetate 
• 6818-10-6 isopropyl α-methoxy-α-phenylacetate 

Relevant academic research and scientific papers

Boron-catalyzed CC functionalization of allyl alcohols

Tris(pentafluorophenyl)borane-catalyzed CC bond functionalization of arylallyl alcohols using donor-acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal-free transformation presents a novel disconnection strategy towards carbon-carbon bond scission and formation.

Chiral-at-Iron Catalyst: Expanding the Chemical Space for Asymmetric Earth-Abundant Metal Catalysis

A new class of chiral iron catalysts is introduced that contains exclusively achiral ligands with the overall chirality being the result of a stereogenic iron center. Specifically, iron(II) is cis-coordinated to two N-(2-pyridyl)-substituted N-heterocycli

Boron-Catalyzed C?C Functionalization of Allyl Alcohols

Tris(pentafluorophenyl)borane-catalyzed C?C bond functionalization of arylallyl alcohols using donor-acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal-free transformation presents a novel disconnection strategy towards carbon-carbon bond scission and formation. (Figure presented.).

Cobalt-Catalyzed Transfer Hydrogenation of α-Ketoesters and N-Cyclicsulfonylimides Using H2O as Hydrogen Source

A Co-catalyzed effective transfer hydrogenation of various α-ketoesters and N-cyclicsulfonylimides by safe and environmentally benign H2O as hydrogen source is described. The reaction used easily available and easy to handle zinc metal as a reductant. Interestingly, the catalytic system does not require ligand for reduction of N-cyclicsulfonylimides. (Figure presented.).

Boron-Catalyzed O-H Bond Insertion of α-Aryl α-Diazoesters in Water

A catalytic, metal-free O-H bond insertion of α-diazoesters in water in the presence of B(C6F5)3·nH2O (2 mol %) was developed, affording a series of α-hydroxyesters in good to excellent yields. The reaction features easy operation and wide substrate scope, and importantly, no metal is needed as compared with the conventional methods. Significantly, this approach further expands the applications of B(C6F5)3 under water-tolerant conditions.

Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio under solvent-free conditions

A highly efficient way for the direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio using a zirconocene complex (1, 1 mol%), a strong Lewis acid of good water tolerance, as a catalyst under solvent-free conditions has been developed. A wide range of acid and alcohol (esters) substrates undergo (trans)esterification to produce carboxylic ester motifs in moderate to good or excellent yields with good functional tolerance, such as that towards C-Br as well as CC and CC bonds. And complex 1 can be recycled six times without showing a significant decline in catalytic efficiency. It was demonstrated that cyclandelate, which is used to treat high blood pressure as well as heart and blood-vessel diseases, can be directly synthesized on a gram scale with 81% yield (6.70 g) using complex 1.

Enantio- and chemoselective Br?nsted-acid/Mg(nBu) 2 catalysed reduction of α-keto esters with catecholborane

The first enantio- and chemoselective Br?nsted-acid catalysed reduction of α-keto esters with catecholborane has been developed. The α-hydroxy esters were obtained under mild reaction conditions in virtually quantitative yields and excellent enantioselectivities. With slight modifications both enantiomers can be obtained without any loss of selectivity. This journal is the Partner Organisations 2014.

Efficient acid-catalyzed conversion of phenylglyoxal to mandelates on flame-derived silica/Alumina

Amorphous, nonporous silica/alumina (SA) made by flame-spray pyrolysis (FSP) efficiently catalyzes the direct conversion of phenylglyoxal (PG) to alkyl mandelates. The SAs exhibited a turnover frequency more than an order of magnitude higher than dealuminated zeolite Y, which hitherto has been considered as the most active solid acid for this reaction. The free diffusion of PG to surface acid sites and rapid removal of mandelate products are proposed to be at the origin of the superior performance of SAs. The recyclability of the catalyst was tested in five repetitive runs and showed no significant loss of catalyst performance.

Asymmetric aerobic oxidation of α-hydroxy acid derivatives catalyzed by reusable, polystyrene-supported chiral N-salicylidene oxidovanadium tert-leucinates

The direct immobilization of two different C-5-propargyl ether-modified, chiral N-salicylidene vanadyl(V) tert-leucinates onto 4-azidomethyl-substituted polystyrene by click chemistry was examined. Among the eight different solvents investigated, the resulting polystyrene-supported catalysts promote the asymmetric, aerobic oxidation of α-hydroxy (thio)esters and amides with enantioselectivities of up to 99% ee (selectivity factor up to 41) in chloroform. These polystyrene-supported catalysts can be readily recovered by filtration and reused for at least four consecutive runs without discernible loss of reactivity and enantioselectivity.

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride in combination with triethylamine: An improved catalytic system for hydroacylation/reduction of activated ketones

A rapid, economic, and high yielding methodology has been developed for hydroacylation/reduction of activated ketones by using 1,3-bis(2,4,6- trimethylphenyl)imidazolium chloride as a catalyst in combination with triethylamine. The reaction proceeded at an ambient temperature via generating N-heterocyclic carbene in situ that interacted with the (hetero)aryl aldehyde employed. While the reduction of ketones takes place in MeOH, the hydroacylation process was found to be effective in THF for both electron rich and deficient aldehydes.