1798-09-0

Usage

Uses

Used in Pharmaceutical and Biomedical Research:
3-Methoxyphenylacetic acid is used as a research compound for studying its presence and role in normal brain tissue. The fluorimetric method developed for its estimation has been applied to analyze its distribution in the caudate nucleus of normal animals, providing insights into its potential biological functions and implications for neurological health.
Used in Analytical Chemistry:
As an off-white solid, 3-Methoxyphenylacetic acid can be utilized in the development and validation of analytical methods for the detection and quantification of related compounds in various samples. This can be particularly useful in the fields of pharmaceuticals, environmental science, and forensic chemistry, where accurate identification and measurement of specific compounds are crucial.
Used in Chemical Synthesis:
3-Methoxyphenylacetic acid can serve as a starting material or intermediate in the synthesis of more complex organic compounds. Its unique structure, featuring a methoxy and carboxy functional group on a phenyl ring, makes it a valuable building block for the creation of novel molecules with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

Purification Methods

Crystallise the acid from H2O, or aqueous EtOH. The S-benzylisothiuronium salt has m 160-161o (from EtOH). [Beilstein 10 I 82, 10 III 428, 10 IV 541.]

InChI:InChI=1/C9H10O3/c1-12-8-4-2-3-7(5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)/p-1

Upstream product

• 82301-50-6 4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one 
• 151-50-8 potassium cyanide 
• 824-98-6 m-methoxybenzyl chloride 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 67-56-1 methanol 
• 143659-24-9 1-Naphthylmethyl 3-methoxyphenylacetate 
• 5020-41-7 2-(3-methoxyphenyl)-ethanol 
• 66947-60-2 5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one 
• 18927-05-4 methyl (3-methoxyphenyl)acetate 
• 621-37-4 m-hydroxyphenylacetic acid 
• 77-78-1 dimethyl sulfate 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 
• 100-84-5 1-methoxy-3-methyl-benzene 

Downstream Products

• 132726-05-7 2-(3-methoxy-phenyl)-5-phenyl-pent-2-en-4-ynoic acid 
• 132593-79-4 6-acetoxy-3-(3-methoxy-phenyl)-coumarin 
• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 5020-41-7 2-(3-methoxyphenyl)-ethanol 
• 36707-27-4 1,2-bis(3-methoxyphenyl)ethane 
• 56438-64-3 1,3-bis(3-methoxyphenyl)propan-2-one 
• 621-37-4 m-hydroxyphenylacetic acid 
• 20341-25-7 (3-methoxy-phenyl)-acetic acid-(3-methoxy-phenethylamide) 
• 73029-52-4 2-(2-iodo-5-methoxyphenyl)acetic acid 
• 6834-42-0 3-methoxyphenylacetic acid chloride 
• 111029-59-5 5,7-diacetoxy-3-(3-methoxy-phenyl)-4-methyl-coumarin 
• 67237-63-2 N-(3,4-dimethoxyphenylethyl)-β-(3'-methoxyphenyl)acetamide 
• 7401-76-5 7-acetoxy-3-(3-methoxy-phenyl)-coumarin 
• 47170-31-0 (3-methoxy-phenyl)-acetic acid 3-morpholin-4-yl-propyl ester 

Relevant academic research and scientific papers

An Efficient and Remarkably Regioselective Synthesis of Benzocyclobutenones from Benzynes and 1,1-Dimethoxyethylene

New efficient methodology for the synthesis of substituted benzocyclobutenones is presented that involves the cycloaddition of various substituted benzynes to 1,1-dimethoxyethylene followed by hydrolysis to the corresponding ketone.In most cases studied a high degree of regioselectivity was observed.These observations are consistent with a nonsynchronous mechanism wherein steric and inductive considerations can be used to account for the products observed.

Visible-light photoredox-catalyzed selective carboxylation of C(sp3)?F bonds with CO2

It is highly attractive and challenging to utilize carbon dioxide (CO2), because of its inertness, as a nontoxic and sustainable C1 source in the synthesis of valuable compounds. Here, we report a novel selective carboxylation of C(sp3)?F bonds with CO2 via visible-light photoredox catalysis. A variety of mono-, di-, and trifluoroalkylarenes as well as α,α-difluorocarboxylic esters and amides undergo such reactions to give important aryl acetic acids and α-fluorocarboxylic acids, including several drugs and analogs, under mild conditions. Notably, mechanistic studies and DFT calculations demonstrate the dual role of CO2 as an electron carrier and electrophile during this transformation. The fluorinated substrates would undergo single-electron reduction by electron-rich CO2 radical anions, which are generated in situ from CO2 via sequential hydride-transfer reduction and hydrogen-atom-transfer processes. We anticipate our finding to be a starting point for more challenging CO2 utilization with inert substrates, including lignin and other biomass.

Visible-Light-Enabled Carboxylation of Benzyl Alcohol Derivatives with CO2 Using a Palladium/Iridium Dual Catalyst

A highly efficient carboxylation of benzyl alcohol derivatives with CO2 using a palladium/iridium dual catalyst under visible-light irradiation was developed. A wide range of benzyl alcohol derivatives could be employed to provide benzylic carboxylic acids in moderate to high yields. Mechanistic studies indicated that the oxidative addition of benzyl alcohol derivatives was possibly the rate-determining-step. It was also found that a switchable site-selective carboxylation between benzylic C?O and aryl C?Cl moieties could be achieved simply by changing the palladium catalyst.

Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions

Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.

Carboxylation of benzylic and aliphatic C-H bonds with CO2 induced by light/ketone/nickel

A photoinduced carboxylation reaction of benzylic and aliphatic C-H bonds with CO2 is developed. Toluene derivatives capture gaseous CO2 at the benzylic position to produce phenylacetic acid derivatives when irradiated with UV light in the presence of an aromatic ketone, a nickel complex, and potassium tert-butoxide. Cyclohexane reacts with CO2 to furnish cyclohexanecar-boxylic acid under analogous reaction conditions. The present photoinduced carboxylation reaction provides a direct access from readily available hydrocarbons to the corresponding carboxylic acids with one carbon extension.

Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2

The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2 to generate important aryl acetic acids is reported. Besides aldehyde hydrazones, a variety of ketone hydrazones, which have not been successfully applied in previous umpolung reactions with other reactive electrophiles, also show high reactivity and selectivity under mild conditions. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and offers easy derivation of important structures, including bioactive felbinac and adiphenine. Computational studies reveal that this umpolung reaction proceeds through the generation of a Ru-nitrenoid followed by concerted [4 + 2] cycloaddition with CO2.

Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts

Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.

Regio- and Stereoselective Oxidation of Styrene Derivatives to Arylalkanoic Acids via One-Pot Cascade Biotransformations

Green and selective oxidation methods are highly desired in chemical synthesis and manufacturing. In this work, we have developed a biocatalytic method for the regio- and stereoselective oxidation of styrene derivatives into arylacetic and (S)-2-arylpropionic acids via a one-pot epoxidation–isomerization–oxidation sequence. This was done via the engineering of Escherichia coli (StyABC-EcALDH) coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI) and aldehyde dehydrogenase (EcALDH) as an active and easily available whole-cell catalyst. Regioselective oxidation of styrene and 11 substituted styrenes using the E. coli cells was performed in a one-pot set-up, producing 12 phenylacetic acids in both high conversion and high yield. Engineering of E. coli (StyABC-ADH9v1) coexpressing SMO, SOI and ADH9v1 (a mutated alcohol dehydrogenase) led to biocatalysts capable of regio- and stereoselective oxidation of α-methylstyrene derivatives to the corresponding chiral acids. One-pot asymmetric synthesis of 4 (S)-2-arylpropionic acids was achieved in good conversion and excellent ee with the E. coli cells. This is a new type of asymmetric alkene oxidation to give chiral acids with no chemical counterpart thus far. The cascade bio-oxidation operates under mild conditions, uses molecular oxygen, exhibits very high regio- and enantioselectivity, and gives high conversion, thus providing a green and efficient method for the synthesis of arylacetic acids and (S)-2-arylpropionic acids directly from easily available styrenes. (Figure presented.).

Nickel-Catalyzed Carboxylation of Benzylic C-N Bonds with CO2

A user-friendly Ni-catalyzed reductive carboxylation of benzylic C-N bonds with CO2 is described. This procedure outperforms state-of-the-art techniques for the carboxylation of benzyl electrophiles by avoiding commonly observed parasitic pathways, such as homodimerization or β-hydride elimination, thus leading to new knowledge in cross-electrophile reactions.

Photogenerated α,n-didehydrotoluenes from chlorophenylacetic acids at physiological pH

Aromatic diradicals are recognized as promising intermediates for DNA cleavage, but their formation has thus far been limited to the Bergman and Myers-Saito cycloaromatizations. We report here the phototriggered generation of all isomers of the potential DNA-cleaving α,n-didehydrotoluene diradicals at physiological pH, accomplished by the irradiation of chlorophenylacetic acids under mild conditions. The desired diradicals were formed upon photolysis of the chosen aromatic in aqueous phosphate buffer solution (pH = 7.3), with the consecutive elimination of biologically compatible chloride ion and carbon dioxide. Theoretical simulations reveal that the efficient decarboxylation of the primarily generated phenyl cations involves a previously not known diradical structure.