4847-64-7

Upstream product

• 488-17-5 3-methylbenzene-1,2-diol 
• 13031-53-3 3-hydroxy-2-phenyl-1H-inden-1-one 
• 95-48-7 ortho-cresol 

Downstream Products

• 1026685-64-2 C₁₄H₁₆O₆ 
• 27320-85-0 3,4-Diacetoxy-5-(2-acetylaminoethylthio)-toluol 
• 488-17-5 3-methylbenzene-1,2-diol 
• 1016-59-7 1-methyl-phenazine 

Relevant academic research and scientific papers

An environmentally friendly electrochemical method for synthesis of benzofuranoquinone derivatives

Electrochemical oxidation of catechols (1a-c) has been studied in the presence of 2-hydroxy-1,4-naphtoquinone (3b) in aqueous solutions, using cyclic voltammetry and controlled-potential coulometry. The results indicated that the electrochemically generated o-benzoquinones (2a-c) participate in Michael addition reaction with 3b to the corresponding benzofuranoquinones (8a-c, 10a-c). The electrochemical synthesis of these compounds has been successfully preformed at a carbon rod electrode with good yields using an environmentally friendly method.

Spectrophotometric determination of the stability constant of the inclusion complexes of some catechol derivatives with β-cyclodextrin based on their reaction with iodate

The effects of β-cyclodextrin (β-CD) inclusion on the kinetics of the oxidation of several cathechol derivatives, including 4-tert-butylcatechol, 3-methylcatechol and 3-methoxycatechol, with iodate was studied spectrophotometrically. The rate of the oxida

Application of rank annihilation factor analysis to the determination of the stability constant of the complex XL and rate constants for the reaction of X and XL with the reagent Z using kinetic profiles

A simple procedure tor the kinetic spectrophotometric determination of the formation constant of 1:1 (XL) complexes (or adducts) using rank annihilation factor analysis (RAFA) is proposed. The method was based on the effect of the concentration of L (or X

4,5-Dimethyl-2-Iodoxybenzenesulfonic Acid Catalyzed Site-Selective Oxidation of 2-Substituted Phenols to 1,2-Quinols

A site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers, catalyzed by 4,5-dimethyl-2-iodoxybenzenesulfonic acid with Oxone, has been developed. Natural products such as biscarvacrol and lacinilene C methyl ether could be synthesized efficiently under mild reaction conditions. Furthermore, both the reaction rate and site selectivity could be further improved by the introduction of a trialkylsilylmethyl substituent at the 2-position of phenols. The corresponding 1,2-quinols could be transformed into various useful structural motifs by [4+2] cycloaddition cascade reactions.

Laccase-mediated multi-step homo- and heteromolecular reactions of ortho-dihydroxylated aromatic compounds and mono- or diaminated substances resulting in C-C, C-O and C-N bonds

Three types of reactions involving oxidation, inter- and intramolecular Michael-addition as well as homo-intermolecular dimerization, catalyzed by laccase [E.C. 1.10.3.2] of Pycnoporus cinnabarinus in the presence of oxygen, resulted in the formation of dimeric, trimeric and cyclic products with yields up to 44% (non-optimized reactions). For heteromolecular reactions a number of different aminated five- and six-membered aromatic compounds were used. The first reaction type involved the oxidation of catechol, 3- or 4-methylcatechol to o-quinone and subsequent Michael-addition of the amino compounds with C-N bond formation. Conclusive analytical data (UV-vis data, MS spectra) for the respective o-quinone are provided. The second type of reaction included a homo-intermolecular dimerization probably with C-C and C-O bond formation to the proposed dibenzofuran derivatives. The heteromolecular reaction with the amino compounds yielded trimers consisting of homomolecular dimers and the amino compound connected via a C-N bond. The third reaction type started from epinephrine (adrenaline) which was oxidized by laccase and underwent an intramolecular Michael-addition to adrenochrome. The subsequent heteromolecular reaction resulted in the unusual substance class of cyclooctenes (diazocines). Differences between the reaction types in regard to the kind of o-hydroquinone, amino compound used and the types of product recovered are discussed.

One-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity

A commercial laccase, Suberase from Novozymes, was used to catalyse the synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives. The yields were, in some cases, similar to or better than that obtained by other enzymatic, chemical or electr

Electrochemical oxidation of catechols (=benzene-1,2-diols) in the presence of benzoylacetonitrile: Synthesis of new derivatives of 5,6-dihydroxybenzofuran

The electrochemical oxidation of catechol (=benzene-1,2-diol; 1a) and some of its derivatives in H2O/MeCN 1: 1 containing benzoylacetonitrile (=β-oxobenzenepropanenitrile; 3) as a nucleophile was studied by cyclic voltammetry and controlled-potential coulometry. The voltammetric data showed that electrochemically generated o-benzoquinones (=cyclohexa-3,5-diene-1,2- diones) from catechol (1a) and 3-methylcatechol (1b) participate in a Michael-addition reaction with 3 to form the corresponding 5,6- dihydroxybenzofuran-3-carbonitrile 8 (Scheme1). In this work, we report an efficient one-pot method with high atom economy for the synthesis of new substituted 5,6-dihydroxybenzofuran-3-carbonitriles in an undivided cell under ambient conditions.

Facile one-pot synthesis of 2-(3,4-dihydroxyphenyl)-2-phenyl-2H-indene derivatives via electrochemical oxidation of catechols in the presence of 2-phenyl-1,3-indandione

The electrooxidation of 3-substituted catechols (1a-1c) has been studied in the presence of 2-phenyl-1,3-indandione (3) in water + acetonitrile (90/10 v/v) solution, using the electrochemical and spectroelectrochemical methods. The o-benzoquinones (2a-2c) derived from catechols (1a-1c) precipitate out according to Michael addition reactions with 2-phenyl-1,3-indandione (3) to form the corresponding 2-(3,4-dihydroxyphenyl)-2-phenyl-2H-indene derivatives (5a-5c). An EC mechanism was proposed for the electrode process. The efficient electrochemical syntheses of the new catechol derivatives (5a-5c) were performed at a carbon rod electrode in an undivided cell at high yields.

Multiple Electron Oxidation of Phenols by an Oxo Complex of Ruthenium(IV)

The kinetics of oxidation of phenol and alkylated phenol derivatives by (2+) and (2+) (bpy is 2,2'-bipyridine and py is pyridine) to give the corresponding quinones have been studied in aqueous solution and in acetonitrile.The reactions are first order in both phenol and Ru(IV)=O(2+) or Ru(III)-OH(2+).They proceed via a detectable intermediate, which is a Ru(II) complex. 18O isotopic labeling experiments show that transfer of the oxo group from Ru(IV)=O(2+) to phenol is quantitative.The reactions are facile.With Ru(IV)=O(2+) as oxidant k(25 deg C, CH3CN) = 1.9 (+/-0.4) E2M-1s-1; with Ru(III)-OH(2+) as oxidant k(25 deg C, CH3CN) = 4.0 (+/-0.4) E1M-1s-1.On the basis of the rate laws, the magnitude of OH/OD and CH/CD kinetic isotope effects, and the 18O labeling results, the most reasonable mechanisms for oxidation of phenol by Ru(IV)=O(2+) appears to be electrophilic attack on the aromatic ring.For Ru(III)-OH(2+), oxidation appears to occur by CH/H atom transfer in CH3CN and OH/H atom transfer in water.

Kinetics of V(IV) Catalysed Oxidation of Phenols by Acid Bromate

The oxidation of phenol and substituted phenols was studied using KBrO3 as oxidant in presence of V(IV) in binary solvent mixtures of acetic acid in water.Order with respect to oxidant is one and the order with respect to substrate and the catalyst is found to be fractional.The behaviour of acid shows that the order in acid is different under different acid concentrations.Effects of temperatures and percentage composition of acetic acid were studied.A suitable mechanism in presence of catalyst is given explaining the experimental facts.The effect of substituents was also studied and discussed.