18584-23-1

Basic information

• Product Name: hydroxy-p-tolyl-acetic acid ethyl ester
• Synonyms: hydroxy-p-tolyl-acetic acid ethyl ester
• CAS NO: 18584-23-1
• Molecular Weight: 194.23
• Mol File: 18584-23-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: hydroxy-p-tolyl-acetic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: hydroxy-p-tolyl-acetic acid ethyl ester(18584-23-1)
• EPA Substance Registry System: hydroxy-p-tolyl-acetic acid ethyl ester(18584-23-1)

Safety Data

• Hazardous Substances Data: 18584-23-1(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 18584-20-8 4-methylmandelic acid 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 66985-49-7 2-(4-methylphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 14062-19-2 p-tolylacetic acid ethyl ester 
• 27668-90-2 p-methylphenyldiazoacetic acid ethyl ester 
• 924-44-7 glyoxylic acid ethyl ester 
• 108-88-3 toluene 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 4815-10-5 2-hydroxy-2-(4-methylphenyl)acetonitrile 
• 1019019-27-2 2-Hydroxy-2-p-tolyl-acetimidic acid ethyl ester 

Downstream Products

• 18584-20-8 4-methylmandelic acid 
• 90915-35-8 2-amino-5-p-tolyl-oxazol-4-one 
• 88920-26-7 ethoxy-p-methylphenylacetic acid 
• 128839-55-4 ethyl 2-fluoro-2-(4'-methylphenyl)acetate 
• 67593-03-7 2-(2-Ethoxycarbonylmethyl-5-methyl-phenyl)-propionic acid ethyl ester 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 79309-66-3 ethoxy-p-tolyl-acetic acid ethyl ester 
• 1399983-76-6 (E)-ethyl 2-hydroxy-5,9-dimethyl-2-p-tolyldeca-4,8-dienoate 
• 1399983-70-0 ethyl 2-hydroxy-5-methyl-2-p-tolylhex-4-enoate 
• 194937-63-8 ethyl α-methoxy-p-tolylacetate 
• 29266-40-8 (3-methyl-4-oxo-5-p-tolyl-oxazolidin-2-ylidene)-acetic acid ethyl ester 
• 29266-44-2 (3-ethyl-4-oxo-5-p-tolyl-oxazolidin-2-ylidene)-acetonitrile 
• 29266-43-1 (3-methyl-4-oxo-5-p-tolyl-oxazolidin-2-ylidene)-acetonitrile 
• 104-87-0 4-methyl-benzaldehyde 

Relevant articles and documents

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase

Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.

Iron-catalyzed hydrogenation for the in situ regeneration of an NAD(P)H model: Biomimetic reduction of α-Keto-/α-iminoesters

Two irons for a smoother finish: An NAD(P)H model was regenerated readily in situ by iron-catalyzed reduction with molecular hydrogen. The subsequent biomimetic reduction of α-keto-/ α-iminoesters proceeded smoothly in the presence of an iron-based Lewis acid (LA) to provide α-hydroxyesters and amino acid esters in good to excellent yields (see scheme; NAD(P) +=nicotinamide adenine dinucleotide (phosphate), TM=transition metal). Copyright

Simple and efficient synthesis of racemic substituted mandelic acid esters from nonactivated arenes and ethyl glyoxylate

Direct synthesis of racemic aromatic α-hydroxyacetic acid esters via Friedel-Crafts reaction of nonactivated, simple arenes with ethyl glyoxylate promoted by SnCl4 or AlCl3 is described. The use of SnCl4 opens a fast access to various alkyl- and aryl-substituted mandelic acids esters at room temperature within two hours in good yield (>80%) and with high regioselectivity. The procedure was successfully employed also for the alkylation of compounds with condensed aromatic rings. Alternative hydroxyalkylations with AlCl3 require longer reaction time and higher temperature to get a good yield.