6295-06-3

Usage

Uses

Used in the Fragrance Industry:
Butyl glyoxylate is used as a scent ingredient and fixative for its ability to enhance and prolong the fragrance of various products. Its fruity odor adds a pleasant aroma, making it a valuable component in creating appealing scents.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, butyl glyoxylate serves as a key intermediate in the synthesis of various organic compounds. Its versatility in chemical reactions allows for the development of new drugs and medicinal products, contributing to advancements in healthcare.
Used in the Production of Organic Compounds:
Butyl glyoxylate is utilized in the synthesis of a range of organic compounds, showcasing its importance in the chemical industry. Its reactivity and functional groups make it a valuable building block for creating diverse chemical products with various applications.

InChI:InChI=1/C6H10O3/c1-2-3-4-9-6(8)5-7/h5H,2-4H2,1H3

Upstream product

• 87-92-3 (+)-(2R,3R)-dibutyl tartrate 
• 105-76-0 Dibutyl maleate 
• 344268-32-2 dibutyl tartrate 
• 60484-37-9 n-Butyl Dimethoxyacetate 
• 78733-54-7 2-(carbobutoxy)-5,5-diphenyl-1,3-dioxolan-4-one 
• 62563-15-9 (2S,3S)-dibutyl 2,3-dihydroxysuccinate 
• 141-32-2 acrylic acid n-butyl ester 
• 7397-62-8 butyl glycolate 
• 105-75-9 dibutyl fumarate 
• 78733-50-3 2-(carbobutoxy)-5,5-dimethyl-1,3-dioxolan-4-one 

Downstream Products

• 4541-73-5 2,2-bis-(4-methoxyphenyl)acetic acid 
• 5762-65-2 7-methylquinoxalin-2(1H)-one 
• 5762-64-1 6-methylquinoxaline-2(1H)-one 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 20153-24-6 2,2-bis(3,4-dimethoxyphenyl)acetic acid 
• 110150-31-7 bis-(2,3,4-trimethoxy-phenyl)-acetic acid 
• 102473-49-4 bis-(3,4-diethoxy-phenyl)-acetic acid 
• 83700-81-6 bis-(2,4,5-trimethoxy-phenyl)-acetic acid 
• 55687-19-9 5-chloroquinoxaline-2(1H)-one 
• 21771-86-8 2,2-bis(2,5-dimethoxyphenyl)acetic acid 
• 55687-11-1 6-methoxy-2-chloroquinoxaline 
• 117-34-0 2,2-diphenylacetic acid 
• 20809-78-3 bis-(4-methylphenyl)acetic acid 

Relevant academic research and scientific papers

Photodegradation of butyl acrylate in the troposphere by OH radicals: Kinetics and fate of 1,2-hydroxyalcoxy radicals

The rate constant of the reaction of OH radicals with butyl acrylate was studied for the first time using an atmospheric simulation chamber at 298 K and ～750 Torr of air or nitrogen. The decay of the organics was followed using a gas Chromatograph with a flame ionization detector (GC-FID), and the rate constant was determined using a relative rate method with different references. The obtained average value of (1.80 ± 0.26) × 10-11 cm3 molecule-1 s-1 is in agreement with previous determinations of the rate constants of OH radicals with acrylates and methacrylates in the literature. Additionally, product identification under atmospheric conditions was performed for the first time by the GC-MS technique. Butyl glyoxalate was observed as the degradation product in accordance with the addition of OH to the less substituted carbon atom of the double bond, followed by decomposition of the 1,2-hydroxyalkoxy radicals formed. Room temperature rate coefficient was used to estimate the atmospheric lifetime of the ester studied. Reactivity trends are discussed in terms of the substituent effects and the length of the hydrogenated chain of the ester. The atmospheric persistence of BUAC was calculated taking into account the experimental rate constant obtained. Copyright

Stereoelectronic versus steric tuning in the prins cyclization reaction: Synthesis of 2fi-trans pyranyl motifs

The use of carboalkoxyl allenic alcohol for the efficient synthesis of pyranyl motifs via Prlns cycllzatlon Is described. This method provides easy access to 2,6-trans dlhydropyrans In good yield and high dlastereoselectlvlty.

One-pot multicomponent synthesis of novel 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe3O4 MNPs as highly effective nanocatalyst

The immobilization of sulfonic acid on the surface of Fe3O4 magnetic nanoparticles (MNPs) as a novel acid nanocatalyst has been successfully reported. The morphological features, thermal stability, magnetic properties, and other physicochemical properties of the prepared superparamagnetic core–shell (Fe3O4@PFBA–Metformin@SO3H) were thoroughly characterized using Fourier transform infrared (FTIR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), thermogravimetric analysis–differential thermal analysis (TGA-DTA), atomic force microscopy (AFM), dynamic light scattering (DLS), Brunauer–Emmett–Teller (BET), and vibrating sample magnetometer (VSM) techniques. It was applied as an efficient and reusable catalyst for the synthesis of 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives via a one-pot multiple-component cascade reaction under green conditions. The results displayed the excellent catalytic activity of Fe3O4@PFBA–metformin@SO3H as an organic–inorganic hybrid nanocatalyst in condensation and multicomponent Mannich-type reactions. The easy separation, simple workup, excellent stability, and reusability of the nanocatalyst and quantitative yields of products and short reaction time are some outstanding advantages of this protocol.

Highly efficient and practical aerobic oxidation of alcohols by inorganic-ligand supported copper catalysis

The oxidation of alcohols to aldehydes or ketones is a highly relevant conversion for the pharmaceutical and fine-chemical industries, and for biomass conversion, and is commonly performed using stoichiometric amounts of highly hazardous oxidants. The aerobic oxidation of alcohols with transition metal complex catalysts previously required complicated organic ligands and/or nitroxyl radicals as co-catalysts. Herein, we report an efficient and eco-friendly method to promote the aerobic oxidation of alcohols using an inorganic-ligand supported copper catalyst 1, (NH4)4[CuMo6O18(OH)6], with O2 (1 atm) as the sole oxidant. Catalyst 1 is synthesized directly from cheap and commonly available (NH4)6Mo7O24·4H2O and CuSO4, which consists of a pure inorganic framework built from a central CuII core supported by six MoVIO6 inorganic scaffolds. The copper catalyst 1 exhibits excellent selectivity and activity towards a wide range of substrates in the catalytic oxidation of alcohols, and can avoid the use of toxic oxidants, nitroxyl radicals, and potentially air/moisture sensitive and complicated organic ligands that are not commercially available. Owing to its robust inorganic framework, catalyst 1 shows good stability and reusability, and the catalytic oxidation of alcohols with catalyst 1 could be readily scaled up to gram scale with little loss of catalytic activity, demonstrating great potential of the inorganic-ligand supported Cu catalysts in catalytic chemical transformations.

PROCESS FOR PREPARATION OF ACITRETIN

The present invention provides a process for preparation of {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6- trimethyl)phenyl-3,7-dimethyl-nona-2,4,6,8}tetraenoate, an acitretin intermediate of formula (VI) with trans isomer ≥97%, comprising of reacting 3-formyl-crotonic acid butyl ester of formula (V), substantially free of impurities, with 5-(4-methoxy-2,3,6-trimethylphenyl)-3- methyl-penta-2,4-diene-l-triphenyl phosphonium bromide of formula (IV) and isolating resultant compound of formula (VI), treating the filtrate with iodine for isomerization of the undesired cis intermediate and finally obtaining acitretin (I), with desired trans isomer ≥97%.

POLYGLYOXYLATES, MANUFACTURE AND USE THEREOF

Self-immolative polymers degrade by an end-to-end depolymerisation mechanism in response to the cleavage of a stabilizing end-cap from the polymer terminus. Examples include homopolymers, mixed polymers including block copolymers, suitable for a variety of applications. A polyglyoxylate can be end-capped or capped with a linker as in a block copolymer.

Polyglyoxylates: A versatile class of triggerable self-immolative polymers from readily accessible monomers

Self-immolative polymers, which degrade by an end-to-end depolymerization mechanism in response to the cleavage of a stabilizing end-cap from the polymer terminus, are of increasing interest for a wide variety of applications ranging from sensors to controlled release. However, the preparation of these materials often requires expensive, multistep monomer syntheses, and the degradation products such as quinone methides or phthalaldehydes are potentially toxic to humans and the environment. We demonstrate here that polyglyxoylates can serve as a new and versatile class of self-immolative polymers. Polymerization of the commercially available monomer ethyl glyoxylate, followed by end-capping with a 6-nitroveratryl carbonate, provides a poly(ethyl glyoxylate) that depolymerizes selectively upon irradiation with UV light, ultimately generating ethanol and the metabolic intermediate glyoxylic acid hydrate. To access polyglyoxylates with different properties, the polymerization and end-capping approach can also be extended to other glyoxylate monomers including methyl glyoxylate, n-butyl glyoxylate, and benzyl glyoxylate, which can be easily prepared from their corresponding fumaric or maleic acid derivatives. Random copolymers of these monomers with ethyl glyoxylate can also be prepared. Furthermore, using a multifunctional end-cap that is UV-responsive and also enables the conjugation of another polymer block via an azide-alkyne "click" cycloaddition, amphiphilic self-immolative block copolymers are also prepared. These block copolymers self-assemble into micelles in aqueous solution, and their poly(ethyl glyoxylate) blocks rapidly depolymerize upon UV irradiation. Overall, these strategies are expected to greatly expand the utility of self-immolative polymers by providing access for the first time to self-immolative polymers with tunable properties that can be readily obtained from simple monomers and can be designed to depolymerize into nontoxic products.

Enantioselective Friedel-Crafts reaction of acylpyrroles with glyoxylates catalyzed by BINOL-Ti(IV) complexes

We report the first efficient enantioselective Friedel-Crafts hydroxyalkylation of pyrroles having one electron-withdrawing group at the α, β or N-positions with alkyl glyoxylates catalyzed by readily available chiral BINOL-Ti(IV) complexes (1-5 mol %). The reaction regioselectively led to the desired pyrrole-hydroxyacetic acid derivatives with good yields (70-96%) and enantiomeric excesses up to 96%, and is applicable in multigram scale with low loading of the catalyst (1 mol %).

Highly enantioselective friedel-crafts reaction of thiophenes with glyoxylates: Formal synthesis of duloxetine

An efficient Friedel-Crafts reaction of a series of 2-substituted thiophenes with alkyl glyoxylates has been developed using a catalytic amount of an easy accessible 6,6'-dlbromo-BINOL/TI(IV) complex. A variety of hydroxy(thiophene-2-yl)acetates can be synthesized In high enantioselectivites (92-98% ee) and good yields. This Is the first report on the efficient asymmetric F-C reaction of thiophenes with alkyl glyoxylates. Starting from simple thiophene and n-butyl glyoxylate, we demonstrated the formal synthesis of duloxetine.

Origin of the asymmetric induction in metallosalen-catalyzed reactions of aldehydes

This study investigates, experimentally and computationally, the role played by the structure of the diamine moiety of salen chromium complexes in determining the catalyst conformational equilibrium and, in consequence, the direction of asymmetric induction in metallosalen-catalyzed reactions of aldehydes. The Royal Society of Chemistry 2009.