62191-63-3

Basic information

• Product Name: Benzenepropanoic acid, 2-hydroxy-b-methyl-
• CAS NO: 62191-63-3
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• Mol File: 62191-63-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, 2-hydroxy-b-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, 2-hydroxy-b-methyl-(62191-63-3)
• EPA Substance Registry System: Benzenepropanoic acid, 2-hydroxy-b-methyl-(62191-63-3)

Safety Data

• Hazardous Substances Data: 62191-63-3(Hazardous Substances Data)

Upstream product

• 607-71-6 4-methyl-2H-chromen-2-one 
• 828-90-0 4-Methylcumarinsaeure 
• 18435-75-1 4-methyl-chroman-2-one 

Downstream Products

• 61005-11-6 3-(o-N-Methylcarbamoyloxyphenyl)buttersaeuremethylester 

Relevant articles and documents

Enantioselective cathodic reduction of 4-methylcoumarin: Dependence of selectivity on reaction conditions and investigation of the mechanism

The cathodic reduction of 4-methylcoumarin (1) in acidic methanol/water in the presence of yohimbine leads to formation of a mixture of the hydrogenation product 4-methyl-3,4-dihydrocoumarin (2), with an enantiomeric excess (ee) of (R)-2 of 0-67%, and the hydrodimer 3. The relative yields of 2 and 3 and the ee of 2 depend on a number of experimental parameters such as pH, supporting electrolyte, working potential, and the concentrations of substrate and yohimbine, as demonstrated by a series of preparative-scale experiments. In addition, a series of voltammetric and kinetic measurements were carried out to investigate the influence of the individual experimental parameters. Three mechanistic possibilities have been examined, and by combination of the analytical data with the results of the preparative experiments, a single model is put forward which is in accord with the available results. The main features of the mechanistic model can be summarized as follows: 1) under acidic conditions (pH 2-3) the electroactive species is a complex between 1 and H3O+, the reduction of which leads to an enolic radical; 2) this radical is not reduced at the working potential but tautomerizes into the more easily reduced keto radical or dimerizes; 3) the keto radical is reduced and further protonated; 4) the function of the yohimbineH+ is to catalyze the tautomerization and enantioselectively protonate the final carbanion. Additionally, we conclude that the concentration of yohimbine in the immediate vicinity of the electrode is considerably higher than its stoichiometric concentration. Quantum chemical calculations demonstrate that si protonation of the intermediate anion by yohimbineH+ to give (R)-2 is energetically favored.

THE CONVERSION OF 2,4-DINITRO-6-SEC-BUTYLPHENOL AND ITS ESTERS IN THE

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