4237-50-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-2-(4-methoxyphenyl)-2-phenyl-acetic acid is used as a muscarinic M3 receptor antagonist for the treatment of various conditions. Acting as a muscarinic M3 receptor antagonist, 2-hydroxy-2-(4-methoxyphenyl)-2-phenyl-acetic acid can help in managing symptoms associated with excessive activation of the muscarinic M3 receptors, such as overactive bladder, asthma, and chronic obstructive pulmonary disease (COPD). 2-hydroxy-2-(4-methoxyphenyl)-2-phenyl-acetic acid's ability to block these receptors makes it a valuable asset in the development of new therapeutic strategies for these conditions.

InChI:InChI=1/C15H14O4/c1-19-13-9-7-12(8-10-13)15(18,14(16)17)11-5-3-2-4-6-11/h2-10,18H,1H3,(H,16,17)

Upstream product

• 22711-21-3 4-methoxybenzil 
• 4254-17-5 4-methoxybenzoin 
• 611-94-9 4-Methoxybenzophenone 
• 124-38-9 carbon dioxide 
• 2491-32-9 1-(4-Hydroxyphenyl)-2-phenylethanone 
• 58635-82-8 (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline 
• 928712-61-2 α-Hydroxy-4-methoxy-α-phenylbenzeneacetic acid methyl ester 
• 63007-15-8 trans-(4S,5S)-2-benzoyl-4-(methoxymethyl)-5-phenyl-2-oxazoline 
• 73697-99-1 ((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-(4-methoxy-phenyl)-phenyl-methanol 
• 1023-17-2 4-methoxyphenyl benzyl ketone 

Downstream Products

• 21749-83-7 α-(4-methoxyphenyl)phenylacetic acid 
• 4237-50-7 (R)-2-hydroxy-2-(4-methoxyphenyl)-2-phenylacetic acid 
• 94915-15-8 4-methoxy-benzilic acid-(2-dimethylamino-ethyl ester); hydrochloride 
• 102373-01-3 4-methoxy-benzilic acid-(2-diethylamino-ethyl ester) 
• 66476-03-7 3-hydroxy-4-methoxy-benzophenone 
• 107411-17-6 4-Hydroxy-benzilsaeure 
• 69986-36-3 3-hydroxy-4-methoxybenzilic acid 
• 1137-42-4 4-Hydroxybenzophenone 
• 114618-74-5 (+/-)-phthalic acid mono-[2-hydroxy-2-(4-methoxy-phenyl)-2-phenyl-ethyl ester] 

Relevant academic research and scientific papers

Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide

We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic addition of the resulting carbinol anions to electrophilic carbon dioxide.

Control of Enantioselectivity in Rhodium(I) Catalysis by Planar Chiral Dibenzo[a,e]cyclooctatetraenes

Planar chiral 5,11-disubstiuted dibenzo[a,e]cyclo-octatetraenes (dbCOTs) have been developed as the first useful chiral homologs to dbCOT-ligands for asymmetric applications. Methods enabling the preparation of such compounds on a gram-scale in enantiomerically pure form are described. Evaluated as ligands in rhodium(I)-catalyzed 1,4- and 1,2-arylation reactions, tertiary and quarternary stereogenic centers were formed with excellent yields and selectivities of up to >99 % ee. A catalytic asymmetric synthesis of a key cyclization precursor to (?)-penifulvin A highlights the system in an applied context.

PROCESS FOR THE PREPARATION OF SUBSTITUTED BENZILIC ACID FROM SUBSTITUTED BENZILS

The classical process for the rearrangement of substituted benzil to benzilic acid is performed in the presence of sodium or potassium hydroxide as a base using ethanol-ether as a medium. The reaction requires reflux temperature for complete conversion. However, these bases containing metallic ions and generate metallic containing effluent waste which may require additional expenditure for treatment. Moreover, because of corrosive nature of base, and use of flammable solvent, the safety measures are needed during large scale production. Another method also reported for benzilic acid rearrangement at 380° C. which is practically not feasible. The present invention describes the use of quaternary ammonium hydroxides as a base for the rearrangement of the substituted benzils to benzilc acids. It also avoids the use of solvent and reaction can be carried out at relatively lower temperatures. Because of the solvent free reaction condition it reduces the mass/volume of reaction mixture.

QUINUCLIDINE DERIVATIVES AND THEIR USE AS MUSCARINIC M3 RECEPTOR ANTAGONISTS

Compounds of Formula (I) ; in salt or zwitterionic form wherein R 1, R2, R3 and R4 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor, especially inflammatory or obstructive airways diseases. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

Direct Observation of Ultrafast Decarboxylation of Acyloxy Radicals via Photoinduced Electron Transfer in Carboxylate Ion Pairs

Charge-transfer (CT) photoactivation of the electron donor-acceptor salts of methylviologen (MV2+) with carboxylate donors (RCO2-) including benzilates [Ar2C(OH)CO2-] and arylacetates (ArCH2CO2-) leads to transient [MV.+, RCO2.] radical pairs. Femtosecond time-resolved spectroscopy reveals that the photogenerated acyloxy radicals (RCO2.) rapidly lose carbon dioxide by C-CO2 bond cleavage, in competition with back-electron transfer to restore the original ion pair, [MV2+, RCO2-]. The decarboxylation rate constants for ArCH2CO2. lie in the range (1-2) × 109 s-1, in agreement with previous reports. In striking contrast, the C-CO2 bond scission in Ar2C(OH)CO2. occurs within a few picoseconds (kCC = (2-8) × 1011 s-1). The rate constants for decarboxylation of these donors approach those of barrier-free unimolecular reactions. Thus, real-time monitoring of the decarboxylation of benziloxy radicals represents the means for the direct observation of the transition state for C-C bond scission.

Benzylic Acid Rearrangement in the Solid State

Benzylic acid rearrangements in the solid state were studied and some of them were found to proceed faster than in solution.Although the rearrangement which is initiated by an attack of OH- and then proceeds via radical intermediate was clarified to be similar to that in solution, the effect of alkali metal hydroxide on the rearrangement in the solid state was different from that in solution.

Syntheses of Benzilic Acids through Electrochemical Reductive Carboxylation of Benzophenones in the Presence of Carbon Dioxide

Reaction conditions for the electrochemical synthesis of benzilic acid (2a) under the atmosphere of carbon dioxide was investigated from the preparative points of view.The highest yield of 2a (86percent) was obtained under the following conditions; cathode: mercury, electricity passed: 2.3 F/mol, constant current density: 2.5 mA/cm2, benzophenone (1a) (8.2*10-3 mol), electrolyte(KI, 1.7*10-2 mol) in DNF (50 ml).This method and conditions were applied to the syntheses of twelve benzilic acids (2b-2m) and yielded acids in the range of 10-92percent.The yields were strongly depended on the electronic effect of substituents and benzilic acids were not obtained when the ring substituent was NO2, OH, or Br group.

Asymmetric Addition of Organometallics to Chiral Ketooxazolines. Preparation of Enantiomerically Enriched α-Hydroxy Acids

Addition of Grignard and organolithium reagents to chiral α-ketooxazolines results in α-substituted α-hydroxyoxazoline derivatives which on hydrolytic removal of the chiral auxiliary groups give rise to α-substituted α-hydroxy acids in 30-87 percent enantiomeric excess (ee).Studies on the various parameters (solvents, temperature, substituents) were undertaken to reach optimum asymmetric induction.