20731-95-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester is used as an intermediate for the synthesis of various pharmaceuticals. Its role in this industry is crucial, as it aids in the production of numerous important compounds that contribute to the development of life-saving medications.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester is employed as an intermediate in the synthesis of various agrochemicals. Its contribution to this industry is significant, as it helps in the development of chemicals that are essential for enhancing crop protection and productivity.
Used in Asymmetric Synthesis:
(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester is utilized as a chiral auxiliary in asymmetric synthesis. This application is vital for the creation of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical processes due to their distinct biological activities.
Used in Fine Chemicals Preparation:
(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester also serves as a building block in the preparation of fine chemicals. Its use in this area is important, as it enables the synthesis of high-quality specialty chemicals that are used in a wide range of applications, from fragrances to advanced materials.

Upstream product

• 186581-53-3 diazomethane 
• 13113-71-8 (S)-Atrolactic acid 
• 67-56-1 methanol 
• 69489-14-1 (S)-(+)-2-hydroxy-2-phenylpropanal 
• 31508-44-8 2-phenylpropionic acid methyl ester 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 544-97-8 dimethyl zinc(II) 
• 74-88-4 methyl iodide 
• 266694-57-9 Phenyl-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-methanone 
• 1448000-07-4 C₁₈H₂₂O₅ 
• 124-41-4 sodium methylate 
• 1448000-10-9 (3R,6S)-3-butyl-3-hexanoyl-6-methyl-6-phenyl-1,4-dioxane-2,5-dione 
• 1448000-13-2 C₂₃H₃₀O₅ 
• 1448000-16-5 C₂₆H₃₆O₅ 

Downstream Products

• 26164-23-8 (S)-2-methoxy-2-phenylpropionic acid methyl ester 
• 2406-22-6 (2S)-2-phenylpropane-1,2-diol 
• 857665-65-7 (S)-methyl 2-[(diphenylphosphino)oxy]-2-phenylpropionate 
• 1213228-98-8 C₁₇H₁₅NO₆ 
• 1213228-99-9 C₁₇H₁₅NO₃S 
• 52181-20-1 2-hydroxy-N,2-diphenylpropanamide 
• 1865-29-8 2-phenyl-acrylic acid methyl ester 
• 110272-00-9 diisopropyl 1-(1-methoxy-1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate 
• 110272-01-0 C₂₈H₃₆N₂O₈ 
• 13448-81-2 (S)-methyl atrolactate 
• 13113-71-8 (S)-Atrolactic acid 
• 3966-30-1 (R)-Atrolactic acid 
• 13448-80-1 methyl R-(-)-atrolactate 
• 10487-94-2 Methyl-α-phenyl-α-trifluoracetoxypropionat 

Relevant academic research and scientific papers

Electrocarboxylation of haloacetophenones at silver electrode

Electrocarboxylation of haloacetophenones 1 has been carried out in an undivided cell equipped with silver cathode and Mg sacrificial anode in N,N-dimethylformamide. The electroreduction behavior of these haloacetophenones at the Ag electrode was investig

Oxidation of Methyl Trimethylsilyl Ketene Acetals to α-Hydroxyesters with Urea Hydrogen Peroxide Catalyzed by Methyltrioxorhenium

In the presence of catalytic amounts of MTO, methyltrioxorhenium, methyl trimethylsilyl ketene acetals are oxidized with urea hydrogen peroxide to afford α-hydroxy and α-siloxy esters. On treatment with potassium fluoride, the α-hydroxy esters are obtained in high yields.

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol

The enantioseparation of three hydroxyphenylpropionic acid isomers via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. The racemates of all three acid isomers were successfully separated with high efficiency (0.56–0.84) after single crystallization. For 2-hydroxy-3-phenylpropionic acid 4, the configuration of the less-soluble salt was controlled by the crystallization solvent: the (R)-4 salt was crystallized from water, while 2-propanol afforded the (S)-4 salt. The chiral recognition mechanism of the three acids was discussed based on the crystal structures of the diastereomeric salts.

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.

Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage

The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C-F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditio

Asymmetric Ti-crossed Claisen condensation: Application to concise asymmetric total synthesis of alternaric acid

Asymmetric Ti-crossed Claisen condensation utilizing the dioxane-2,5-dione chiral template and its successful application to total synthesis of chiral alternaric acid are described.

Highly homogeneous stereocontrolled construction of quaternary hydroxyesters by addition of dimethylzinc to α-ketoesters promoted by chiral perhydrobenzoxazines and B(OEt)3

A highly efficient enantioselective addition of Me2Zn to α-ketoesters, assisted by a chiral perhydro-1,3-benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α-hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α-ketoesters are employed. The catalyst can be recovered and reused without loss of activity.

Electrocatalytic carboxylation of aromatic ketones with carbon dioxide in ionic liquid 1-butyl-3-methylimidazoliumtetrafluoborate to α-hydroxy- carboxylic acid methyl ester

A new electrochemical procedure for the electrocatalytic carboxylation of aromatic ketones with carbon dioxide in ionic liquid, 1-butyl-3- methylimidazolium tetrafluoborate (BMIMBF4), to α- hydroxycarboxylic acid methyl ester was investigated for the first time. The electrochemical behavior of acetophenone in BMIMBF4 was studied by cyclic voltammetry with a reduction peak at -1.9 V (vs. Ag). The electrolyses experiments were carried out in an undivided cell under mild conditions without any toxic solvents, catalysts and supporting electrolytes, followed by addition of an alkylating agent, affording the α-hydroxycarboxylic acid methyl ester in a moderate yield (62%). The results showed that the yields were strongly affected by various factors: temperature, current density, charge passed, electrode material and substrate concentration. Moreover, the ionic liquid was successfully recycled for this reaction.

Enantioselective alkynylation of carbonyl compounds with trimethoxysilylalkynes catalyzed by lithium binaphtholate

Enantioselective alkynylation of aldehydes and ketones was accomplished using trimethoxysilylalkynes as alkynylating reagents and lithium 3,3′-diphenylbinaphtholate as a catalyst. Optically active propargylic alcohols were obtained in good to high chemica