5524-56-1

Usage

Uses

Used in Flavor and Fragrance Industry:
ETHYL 4-METHYLBENZOYLFORMATE is used as a flavoring agent and fragrance ingredient for its ability to impart a fruity, floral aroma to food, beverages, and cosmetics. Its pleasant scent and taste make it a valuable addition in enhancing the sensory experience of these products.
Used in Pharmaceutical Industry:
ETHYL 4-METHYLBENZOYLFORMATE is utilized in the synthesis of various pharmaceuticals, serving as a key intermediate in the development of new medications. Its chemical properties allow it to be a versatile component in the creation of different drug formulations.
Used in Organic Chemical Reactions:
As an intermediate in organic chemical reactions, ETHYL 4-METHYLBENZOYLFORMATE plays a crucial role in the synthesis of a range of organic compounds. Its reactivity and stability contribute to the successful completion of various chemical processes.
It is important to handle ETHYL 4-METHYLBENZOYLFORMATE with care due to its potential to cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Proper safety measures should be taken to minimize any adverse effects during its use in different applications.

InChI:InChI=1/C11H12O3/c1-3-14-11(13)10(12)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3

Upstream product

• 4755-77-5 Ethyl oxalyl chloride 
• 108-88-3 toluene 
• 119867-78-6 ethyl 2,6-xylylhydrazono(p-tolyl)acetate 
• 6957-89-7 Ethyl dichloro-(ethoxy)-acetate 
• 14062-19-2 p-tolylacetic acid ethyl ester 
• 106-38-7 para-bromotoluene 
• 95-92-1 oxalic acid diethyl ester 
• 1147869-32-6 ethyl 2-diazo-3-hydroxy-3-(4-chlorophenyl)-3-phenylpropanoate 
• 18584-23-1 hydroxy-p-tolyl-acetic acid ethyl ester 
• 27668-90-2 p-methylphenyldiazoacetic acid ethyl ester 
• 1075-47-4 4-methylphenylglyoxal 
• 762-04-9 Diethyl phosphonate 
• 2999-46-4 Ethyl isocyanoacetate 
• 585526-04-1 N-(4-methoxy-4-methylcyclohexa-2,5-dien-1-ylidene)-4-methylbenzenesulfonamide 

Downstream Products

• 93809-89-3 cyclohexyl-hydroxy-p-tolyl-acetic acid ethyl ester 
• 14062-19-2 p-tolylacetic acid ethyl ester 
• 18584-23-1 hydroxy-p-tolyl-acetic acid ethyl ester 
• 62281-66-7 Ester Ih 
• 79523-76-5 2,3-Di-p-tolyl-2,3-bis-triethylsilanyloxy-succinic acid diethyl ester 
• 114070-30-3 2-Hydroxy-3-methylene-2-p-tolyl-succinic acid 1-ethyl ester 4-methyl ester 
• 93903-22-1 ethyl 2,2-bis(4-methylphenyl)-2-hydroxyacetate 
• 916058-71-4 ethyl [N-(p-methoxyphenyl)imino]-(p-tolyl)acetate 
• 3152-16-7 1-(4-Methylphenyl)maleinsaeureanhydrid 
• 102700-84-5 hydroxy-norborn-5-en-2-yl-p-tolyl-acetic acid-(2-pyrrolidino-ethyl ester) 
• 1013910-54-7 (R)-(-)-ethyl 2-hydroxy-3-nitro-2-p-tolylpropanoate 
• 1070237-16-9 ethyl 2-hydroxy-3-nitro-2-p-tolylpropanoate 

Relevant academic research and scientific papers

Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters

Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re

Stereoselective Synthesis of Dihydrocoumarins via [1,2]-Phospha-Brook Rearrangement in Three-Component Coupling Reaction of α-Ketoesters, o-Quinone Methides, and Dialkyl Phosphites

A highly regio- and diastereoselective approach for the synthesis of phosphate substituted dihydrocoumarins via Br?nsted base catalyzed [1,2]-phospha-Brook rearrangement is reported. The two-step, one-pot Michael addition of α-phosphonyloxy enolates proceeds by coupling of dialkyl phosphite and α-ketoesters to o-quinone methides, followed by an intramolecular cyclization, providing 3,4-dihydrocoumarin frameworks.

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters

By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.

General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling

A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.

Chemo- And diastereoselective synthesis of pyrrolidines from aroylformates and δ-tosylamino enones via P(NMe2)3-mediated reductive amination/base-catalyzed michael addition cascade

A novel P(NMe2)3-mediated tandem (1 + 4) annulation between aroylformates and δ-tosylamino enones has been developed that affords a facile synthesis of functionalized pyrrolidines in moderate to excellent yields with exclusive chemoselectivity and high diastereoselectivity. Mechanistic investigation reveals that the reaction proceeds through an unprecedented P(NMe2)3-mediated reductive amination/base-catalyzed Michael addition cascade. The reaction herein also represents the first study of the reactivity patterns of the Kukhtin-Ramirez adducts toward ambiphilic nucleophile-electrophiles.

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters

A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.

Green preparation method of aryl [alpha]-keto ester compound

The invention discloses a green preparation method of an aryl [alpha]-keto ester compound. The method comprises the specific steps that an [alpha]-diazo compound serves as a reaction raw material, copper sulfate serves as a catalyst, water serves as a solvent, a target product aryl [alpha]-keto ester compound is prepared through a reaction at the temperature of 60 DEG C, the structural general formula of the [alpha]-diazo compound is shown in the specification, and the structural general formula of the correspondingly prepared target product aryl [alpha]-keto ester compound is shown in the specification. The method for synthesizing the target product aryl [alpha]-keto ester compound by catalyzing the [alpha]-diazo compound derivative with copper sulfate has the advantages that the reactioncondition is green and mild, the catalyst is cheap and easy to obtain, the operation is simple and convenient, the yield is relatively high, the universality of a reaction substrate is wide, and thelike.

A short route to access oxaspiro[: N,3,3]propellanes

Novel access to oxaspiro[n,3,3]propellanes has been developed from bicyclic lactones directly prepared by a photochemical hydroxymethylation or alternatively by a three-step sequence. Thanks to the presence of additional hydroxy- and propargylic groups, a second cyclization catalyzed by silver or bismuth salts, led to the propellane structure which was finally transformed into spiranic derivatives by a Simmons-Smith reaction or condensation with α-ketoesters.

Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions

The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase

Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.