13865-21-9

Usage

Uses

Used in Chemical Synthesis:
Butanoic acid, 2-methyl-4-oxo-, methyl ester is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block for the creation of more complex molecules, contributing to the development of new materials and chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Butanoic acid, 2-methyl-4-oxo-, methyl ester is used as a key component in the development of new drugs. Its specific chemical properties enable it to be incorporated into the molecular structure of potential therapeutic agents, enhancing their efficacy and selectivity.
Used in Flavor and Fragrance Industry:
Butanoic acid, 2-methyl-4-oxo-, methyl ester is also utilized in the flavor and fragrance industry due to its distinct aroma and taste. It can be used to create unique scents and flavors for various products, such as perfumes, cosmetics, and the food industry.
Used in Research and Development:
Butanoic acid, 2-methyl-4-oxo-, methyl ester is employed in research and development settings to study its properties and potential applications. Scientists and researchers use it to explore new reaction pathways, develop novel synthetic methods, and investigate its potential use in various fields, including materials science, pharmaceuticals, and environmental applications.

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 3487, 1982 DOI: 10.1016/S0040-4039(00)87648-0

Upstream product

• 25252-24-8 3-methoxycarbonylbutyraldehyde dimethylacetal 
• 201230-82-2 carbon monoxide 
• 80-62-6 methacrylic acid methyl ester 
• 110-91-8 morpholine 
• 73372-15-3 methyl 4-hydroxy-2-methylbutanoate 
• 130450-06-5 2-(2,2-Dimethoxy-ethyl)-2-methyl-malonic acid dimethyl ester 
• 51534-81-7 dimethyl 2-(2,2-dimethoxyethyl)-1,3-propanedioate 
• 124-41-4 sodium methylate 
• 57976-71-3 trans-2,2-dichloro-3-methylcyclopropanecarbaldehyde 
• 127590-16-3 1-Methyl-2-trimethylsilanyloxy-cyclopropanecarboxylic acid methyl ester 
• 554-12-1 propanoic acid methyl ester 
• 85684-59-9 percarbonate de O,O-t-butyle et O-vinyle 

Downstream Products

• 73372-15-3 methyl 4-hydroxy-2-methylbutanoate 
• 1679-47-6 3-methyltetrahydro-2-furanone 
• 70423-38-0 (S)-2-methyl-1,4-butandiol 
• 2938-98-9 (R)-2-methylbutane-1,4-diol 

Relevant academic research and scientific papers

SYNTHESE D'ALDEHYDES γ-FONCTIONNELS PAR VOIE RADICALAIRE

The addition of radicals issued from the solvent to the double bond of O,O-t-butyl and O-vinyl peroxycarbonate results on the free-radical induced decomposition of this peroxyester and offers an original synthetic route for γ-functional aldehydes.

Efficient synthesis of chiral γ-aminobutyric esters: Via direct rhodium-catalysed enantioselective hydroaminomethylation of acrylates

The successful rhodium catalysed asymmetric intermolecular hydroaminomethylation (HAM) of alkenes using a single catalyst bearing the (R,R)-QuinoxP? ligand is reported. The HAM of α-alkyl acrylates is revealed to be an efficient tool for the regio- and en

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Synthesis of β2,2-Amino Esters via Rh-Catalysed Regioselective Hydroaminomethylation

The synthesis of β2,2-amino esters was successfully achieved via Rh-catalysed regioselective hydroaminomethylation of methyl methacrylate with secondary amines using the neutral precursor [Rh(acac)(CO)2]. In this process, the presence of molecular sieves revealed crucial in order to access the final amino ester. For the synthesis of products containing aniline derivatives, the use of the cationic precursor [Rh(COD)2]BF4 and MeCgPPh phosphine as ligand was necessary in a mixture of toluene/DCE as solvent. Effects of the steric and electronic properties of the amines were observed during this study. Interestingly, poisoning effect of CO in the hydrogenation of the imine intermediate was observed when benzyl amine was used. (Figure presented.).

α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation

Hydroformylation utilizes dihydrogen, carbon monoxide, and a catalyst to transform alkenes into aldehydes. This work applies chiral bisdiazaphospholane (BDP)- and bisphospholanoethane-ligated rhodium complexes to the hydroformylation of a variety of alkenes to produce chiral tetrasubstituted aldehydes. 1,1′-Disubstituted acrylates bearing electron-withdrawing substituents undergo hydroformylation under mild conditions (1 mol % of catalyst/BDP ligand, 150 psig gas, 60 °C) with high conversions and yields of tetrasubstituted aldehydes (e.g., 13:1 regioselectivity, 85% ee, and 99% regioselectivity and >19:1 diastereoselectivity to tetrasubstituted aldehydes at rates >50 catalyst turnovers/hour. NMR studies of the noncatalytic reaction of HRh(BDP)(CO)2 with methyl 1-fluoroacrylate enable interception of tertiary alkylrhodium intermediates, demonstrating migratory insertion to acyl species is slower than formation of secondary and primary alkylrhodium intermediates. Overall, these investigations reveal how the interplay of sterics, electronics, and ring strain are harnessed to provide access to valuable α-tetrasubstituted aldehyde synthetic building blocks by promoting branched-selective hydroformylation.

Synthesis of meta-substituted monodentate phosphinite ligands and implication in hydroformylation ?

Abstract: Synthesis of meta-substituted phosphinite ligands 3,3′-(methoxyphosphanediyl)bis(N,N- diethylaniline) (4a) and methoxybis(3-methoxyphenyl)phosphane (4b), in high yields, has been demonstrated. Typical phosphorus chemical shift between 110–120 ppm, appearance of methoxy protons and corresponding carbon, as well as ESI-MS spectra unambiguously confirmed the existence of phosphinite ligands 4a and 4b. To demonstrate the synthetic usefulness of 4a and 4b, these ligands were tested in the rhodium catalyzed hydroformylation of 1-octene. The diethylamine substituted ligand 4a was found to be highly active, whereas 4b was less reactive but revealed slightly better regioselectivity of 62% under optimized conditions. Additionally, 4a and 4b were found to catalyze the hydroformylation of styrene, 1-undecenol and 1,1-disubstituted functional olefin, methyl methacrylate. Both the ligands displayed excellent conversion of styrene, and 4b revealed an excellent branch selectivity of 75%. Although 1-undecenol proved to be amenable to hydroformylation (85–90% conversion to aldehyde), both the ligands failed to discriminate between the linear and branched products. Substrate methyl methacrylate proved to be highly challenging and reduced conversion (between 33–42%) was observed under optimized conditions. Ligand 4a was found to be highly selective towards linear aldehyde (81% linear selectivity). Graphical Abstract: Synopsis Two step synthetic protocol to access meta-substituted monodentate phosphinite ligands 3,3′-(methoxyphosphanediyl)bis(N,N-diethylaniline) (4a) and methoxybis(3-methoxyphenyl)phosphane (4b) has been developed and the ligands have been fully characterized. Apart from catalyzing the hydroformylation of benchmark substrates 1-octene and styrene, 4a and 4b were found to catalyze the hydroformylation of 1-undecenol, a functional olefin and a highly challenging 1,1-disubstituted functional olefin methyl methacrylate. [Figure not available: see fulltext.].

METHOD FOR PRODUCING α-METHYL-γ-BUTYROLACTONE

PROBLEM TO BE SOLVED: To provide a producing method capable of obtaining a high-purity α-methyl-γ-butyrolactone. SOLUTION: There is provided a method for producing α-methyl-γ-butyrolactone, in producing α-methyl-γ-butyrolactone represented by following formula (1), including the steps of: adding an organic base or a salt thereof into a reaction liquid; and distilling the reaction liquid. COPYRIGHT: (C)2015,JPOandINPIT

Highly regioselective osmium-catalyzed hydroformylation

The first highly regioselective and general osmium-catalyzed hydroformylation of olefins to aldehydes is reported. The combination of Os3(CO)12 and imidazoyl-substituted phosphine ligands allows n-selective (up to 99%) hydroformylation of bulk aliphatic as well as functional alkenes in good yields (64-87%). This journal is

A bulky phosphite modified rhodium catalyst for efficient hydroformylation of disubstituted alkenes and macromonomers in supercritical carbon dioxide

The hydroformylation of disubstituted alkenes and related macromonomers in supercritical CO2 is demonstrated. Higher turnover frequencies were observed for the 1,2-disubstituted alkenes than for the 1,1-disubstituted alkenes. The turnover frequency for poly(styrene) macromonomer hydroformylation compares well with that observed for cyclohexene. The turnover frequency observed for poly(methyl methacrylate) macromonomer hydroformylation is considerably lower than that observed for methyl methacrylate. Unprecedented turnover frequencies are observed in comparison with previous studies where CO2 has been applied as a solvent. This is achieved using rhodium modified with a readily available bulky phosphite ligand without the need of ligand modification to improve solubility in supercritical CO2.

OPTICALLY ACTIVE PHOSPHITES AND PHOSPHORAMIDITES BEARING BIPHENOL SKELETONS WITH AXIAL CHIRALITY, AND THEIR USE IN CATALYTIC ASYMMETRIC REACTIONS

Novel optically active ligands which are mondentate phosphites and phosphoramidites, and bidentate phosphites and phosphoramidites; optically active catalysts comprising a reaction mixture of the ligand and a transition metal or its compound; and processes of using the optically active catalysts to produce optically active compounds.