93-25-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxyphenylacetic acid is used as a pharmaceutical intermediate for its cytotoxic properties, which can be harnessed in the development of drugs targeting specific diseases and conditions. Its unique chemical structure allows for the synthesis of various pharmaceutical compounds, contributing to the advancement of medicine.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1930, 1948 DOI: 10.1021/ja01185a084

Purification Methods

Crystallise the acid from H2O, EtOH or aqueous EtOH, pet ether/Et2O and dry it in a vacuum desiccator over Sicapent. The amide has m 131o (from EtOH). [Beilstein 10 H 188, 10 III 422, 10 IV 536.]

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

Upstream product

• 142-82-5 n-heptane 
• 578-58-5 2-methylmethoxybenzene 
• 1822-71-5 n-pentylsodium 
• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 49711-50-4 2-cyano-3-(2'-methoxy-1'-phenyl)acrylic acid 
• 121985-99-7 2-hydroxy-2-(2-methoxyphenyl)acetonitrile 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 74-88-4 methyl iodide 
• 109-66-0 pentane 
• 27798-60-3 methyl 2-(2-methoxyphenyl)acetate 
• 124-38-9 carbon dioxide 
• 108-24-7 acetic anhydride 
• 100-66-3 methoxybenzene 
• 90585-32-3 1,1-dibromo-2-(2-methoxyphenyl)ethene 

Downstream Products

• 55801-78-0 2'-nitro-2-methoxy-trans-stilbene 
• 27798-60-3 methyl 2-(2-methoxyphenyl)acetate 
• 96687-73-9 Methyl (S)-(+)-2-(2-methoxyphenyl)propanoate 
• 124028-83-7 6-fluoro-3-(2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-4-carboxylic acid 
• 110191-35-0 4-Benzyloxy-2-(2-methoxy-benzyl)-7-methyl-1H-benzoimidazole 
• 74384-27-3 (2-Methoxy-phenyl)-acetic acid o-tolyl ester 
• 74384-29-5 (2-Methoxy-phenyl)-acetic acid 2,4-dimethyl-phenyl ester 
• 82082-46-0 N-Benzyl-2-(2-methoxy-phenyl)-acetamide 
• 63730-75-6 tert-butyl α-(2-methopxyphenyl)acetate 
• 92549-46-7 1-(2,4-dihydroxy-phenyl)-2-(2-methoxy-phenyl)-ethanone 
• 22532-50-9 Acetic acid 2-(2-methoxy-phenyl)-ethyl ester 
• 273720-79-9 (E)-2-methoxy-α-(2-methoxyphenyl)cinnamic acid 
• 135-02-4 ortho-anisaldehyde 
• 2569-75-7 7-Hydroxy-2,3-dimethylchromone 

Relevant academic research and scientific papers

Method for preparing carboxylic acid by one-pot method

The invention discloses a method for preparing carboxylic acid by a one-pot method, which comprises the steps of carrying out a Corey-Fuchs process on 1,1-dibromo olefin under the action of n-butyllithium, reacting with isopropanol pinacol borate, quenching with hydrogen chloride, oxidizing with an oxidant, separating and purifying to obtain carboxylic acid. The method disclosed by the invention is a one-pot preparation method, is simple and convenient to operate, does not need to use metal catalysis, uses cheap and easily available reagents for reaction, is green and environment-friendly, hasmild reaction conditions and wide substrate applicability, and provides a new way for rapidly preparing a series of carboxylic acids containing different functional groups.

Synthetic method of benzofuranone

The invention provides a synthetic method of benzofuranone. According to the method, o-cresol which is relatively easy to obtain is used as an initial raw material, and the target product benzofuranone is prepared through four-step reaction; and the whole preparation process is mild in condition, high in yield, easy to operate, small in environmental pollution and suitable for large-scale industrial production.

Bimane: A Visible Light Induced Fluorescent Photoremovable Protecting Group for the Single and Dual Release of Carboxylic and Amino Acids

A series of ester conjugates of carboxylic and amino acids were synthesized based on bimane fluorescent photoremovable protecting group (FPRPG). The photorelease of single and dual (same as well as different) carboxylic and amino acids is demonstrated from a single bimane molecule on irradiation with visible light (λ ≥ 410 nm). The detailed mechanistic study of photorelease revealed that the release of two caged acids is simultaneous but in a stepwise pathway.

Methoxyphenylacetic acid, intermediate thereof, and preparation method of salt thereof

The invention discloses methoxyphenylacetic acid, an intermediate thereof, and a preparation method of a salt thereof. The invention provides a preparation method of hydroxyl phenylacetate, wherein the method may be a method (1) or a method (2). The method has high yield, high purity, simple operation process, mild reaction conditions, short reaction time and low demand on equipment. A catalyst in the method is recyclable, so that the method has simple post-treatment. The method is environment-friendly, is low in production cost and is suitable for industrial production.

Photocaging of Single and Dual (Similar or Different) Carboxylic and Amino Acids by Acetyl Carbazole and its Application as Dual Drug Delivery in Cancer Therapy

A new fluorescent photoremovable protecting group (FPRPG) based on acetylcarbazole framework has been explored for the first time release of single and dual (similar or different) substrates from single chromophore. Mechanistic studies of the photorelease process revealed that photorelease of two (similar or different) substrates from acetyl carbazole proceeds via a stepwise pathway. Further, we constructed photoresponsive dual drug delivery system (DDS) to release two different anticancer drugs (caffeic acid and chlorambucil, 1 equiv each). In vitro study reveals that our DDS exhibit excellent properties like biocompatibility, cellular uptake, and photoregulated dual drug release.

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.

Metal-free, catalytic regioselective oxidative conversion of vinylarenes: A mild approach to phenylacetic acid derivatives

A new synthetic approach towards the synthesis of phenylacetic acids from aromatic alkenes has been developed for the first time under mild conditions by employing non-toxic reagents such as molecular iodine and oxone. This metal-free catalytic regioselective oxygenation of vinylarenes proceeds via tandem iodofunctionalization/de-iodination induced rearrangement.

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.

Controlled anion migrations with a mixed metal Li/K-TMP amide: General application to benzylic metalations

A general method is described for benzylic metalation of o-, m-, and p-substituted toluenes using a mixed metal amide base generated from BuLi/KOtBu/TMP at -78 °C in THF. The excellent selectivity achieved can be rationalized by the ability of the mixed metal amide base to facilitate an anion migration from the kinetic (o-aryl) to the benzylic metalation site. Remarkably, this controlled anion migration is achievable with catalytic amounts of TMP at -78 °C.