2612-02-4

Usage

Uses

Used in Mass Spectrometry Applications:
5-Methoxysalicylic acid is used as a matrix additive in matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) for enhancing the electrical conductivity of the matrix crystal. This application is particularly relevant for the analysis of Fusarium species through intact spore mass spectrometry.
Used in Oligonucleotides Analysis:
A mixture of 5-methoxysalicylic acid and spermine can be employed as a matrix for oligonucleotides analysis in MALDI mass spectrometry, providing a useful tool for studying nucleic acid structures and interactions.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 2301, 1950 DOI: 10.1021/ja01161a530

InChI:InChI=1/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)/p-1

Upstream product

• 186581-53-3 diazomethane 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 62536-85-0 2-acetoxy-5-methoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 2785-98-0 2,5-dimethoxybenzoic acid 
• 586-38-9 3-Methoxybenzoic acid 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 298-14-6 potassium hydrogencarbonate 
• 150-76-5 4-methoxy-phenol 
• 1315577-29-7 C₁₅H₂₆O₃Si 
• 6280-89-3 2-chloro-5-methoxybenzoic acid 
• 41951-76-2 2-hydroxy-5-methoxybenzyl alcohol 
• 71917-43-6 2-Hydroxy-2-(2-hydroxy-5-methoxy-phenyl)-indan-1,3-dione 

Downstream Products

• 2905-82-0 methyl 5-methoxy-2-hydroxybenzoate 
• 529-49-7 gentitein 
• 491-64-5 isogentisine 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 106203-26-3 2-(4'-fluorophenoxy)-5-methoxybenzoic acid 
• 86456-12-4 2-(3-chlorophenoxy)-5-methoxybenzoic acid 
• 86456-23-7 2-(5-chloro-2-methylphenoxy)-5-methoxybenzoic acid 
• 171016-57-2 (2-Hydroxy-5-methoxy-phenyl)-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-methanone 
• 41951-76-2 2-hydroxy-5-methoxybenzyl alcohol 
• 3410-94-4 4-methoxy-2,6-dinitrophenol 
• 132020-40-7 3-bromo-2-hydroxy-5-methoxy-benzoic acid 
• 437-50-3 gentisin 
• 13379-35-6 1-hydroxy-3,7-dimethoxyxanthone 
• 17336-15-1 5-methoxyaspirin 

Relevant academic research and scientific papers

Synthesis of salicylic acid derivatives in presence of ultrasonic irradiation using water as solvent

An improved synthesis of salicylic acid using ultrasonic irradiation and water as solvent can be achieved with copper and pyridine as catalysts. A number of salicylic acids were prepared in good yield and in a short reaction time.

Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids

A simple Pd(OAc)2 catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant has been explored. This protocol features relatively broad substrate scope and operational simplicity. The compatibility of ortho-substituted substrates is an effective complement to the previous ortho-hydroxylation reaction.

Catalytic oxidation of alcohols and alkyl benzenes to carbonyls using Fe3O4?SiO2?(TEMPO)-: Co -(Chlorophyll-CoIII) as a bi-functional, self-co-oxidant nanocatalyst

Chlorophyll b was extracted from heliotropium europaeum plant, demetalated, allylated and grafted to acrylated TEMPO through a copolymerization protocol. Then, the chlorophyll monomers were coordinated to Co ions, immobilized on magnetic nanoparticles and the resulting hybrid was used as a powerful catalyst for a variety of oxidation reactions. By using the present method, oxidation of benzylic alcohols and alkyl benzenes to carbonyls was accomplished in water under aerobic conditions. Moreover, direct oxidation of alcohols to carboxylic acids was performed by adding NaOCl to the mixture. All entries were oxidized to the corresponding desired product with high to excellent yields and up to 97% selectivity. The catalyst was thoroughly characterized by CV, TGA, VSM, XRD, XPS, DLS, FE-SEM, TEM, UV-Vis, EDX, and BET analyses. The activity of the catalyst was investigated by applying various components of the catalyst to the oxidation model separately. The reasonable mechanisms are suggested based on the cooperation between the TEMPO groups and cobalt(iii) (or Co(iv)) sites on the catalyst. The catalyst could be recovered and reused for at least 7 consecutive recycles without any considerable reactivity loss. This journal is

Fe3O4@SiO2@Im[Cl]Mn(III)-complex as a highly efficient magnetically recoverable nanocatalyst for selective oxidation of alcohol to imine and oxime

An efficient and environmentally friendly oxidation process for the one-pot preparation of oxime, imine and carbonyl compounds through alcohol oxidation in the presence of H2O2 and/or O2 have been developed by a melamine-Mn(III) Schiff base complex supported on Fe3O4@SiO2–Cl nanoparticles, named as Fe3O4@SiO2@Im[Cl]Mn(III)-complex nanocomposite, at room temperature. Direct oxidation of alcohol to carboxylic acid was performed using the catalyst in the presence of molecular O2 at room temperature in a different approach. The oxidation products were obtained with excellent yields and high TOFs. The properties of the catalyst were characterized by Fourier transform infrared spectroscopy (FTIR), elemental analysis (C, H, N), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), inductive coupled plasma (ICP), cyclic voltammetry (CV), nuclear magnetic resonance (1H & 13C NMR), vibration sample magnetometer (VSM), Brunauer– Emmett–Teller (BET) and differential pulse voltammetry (DPV) analyses. The mechanism of the oxidation processes was investigated for the both H2O2 and O2 oxidants. The role of the imidazolium moiety in the catalyst as a secondary functionality was investigated. Chemoselectivity behavior of the catalyst was studied by some combinations. The catalyst could be recycled from the reaction mixture by a simple external magnet and reused for several times without any considerable reactivity loss.

A versatile approach for the synthesis of para -substituted arenes via palladium-catalyzed C-H functionalization and protodecarboxylation of benzoic acids

While a great number of ortho C-H functionalization reactions have been developed and several breakthroughs have been achieved in meta C-H activation, para C-H functionalization is still in its infancy stage. In this article, a versatile strategy for the synthesis of para-substituted arenes has been developed via a tandem process consisting of palladium-catalyzed C-H functionalization and subsequent copper-catalyzed protodecarboxylation of benzoic acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the para positions of arenes bearing a variety of substituents.

General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation

A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.

Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction

The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense of bicarbonate as CO2 source is reported. In contrast to the classic Kolbe-Schmitt reaction, the biocatalytic equivalent proceeded in a highly regioselective fashion exclusively at the ortho-position of the phenolic directing group in up to 80% conversion. Several enzymes were identified, which displayed a remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino- functionalities. Based on the crystal structure and molecular docking simulations, a mechanistic proposal for 2,6-dihydroxybenzoic acid decarboxylase is presented.

PD(II)-CATALYZED HYDROXYLATION OF ARENES WITH O2 OR AIR

Pd (II) -catalyzed ortho-hydroxylat ion of variously substituted aromatic carboxylic acids under O2 or air is achieved under non-acidic conditions. Extensive labeling studies support a direct oxygenation of aryl C-H bonds with molecular oxygen.

Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O2 or air

(Chemical Equation Presented) Pd(II)-catalyzed ortho-hydroxylation of variously substituted benzoic acids under 1 atm of O2 or air is achieved under nonacidic conditions. Extensive labeling studies support a direct oxygenation of aryl C-H bonds with molecular oxygen.

Process for the synthesis of hydroxy aromatic acids

Hydroxy aromatic acids are produced in high yields and high purity (>95%) from halogenated aromatic acids in a reaction mixture containing a copper source and a ligand that coordinates to copper.