86358-29-4

Usage

Uses

Used in Flavoring and Fragrance Industry:
ETHYL 3-METHOXYBENZOYLFORMATE is used as a flavoring agent and fragrance ingredient in the food and cosmetic industries. Its sweet, floral scent and taste make it a valuable addition to these products, enhancing their sensory appeal.
Used in Pharmaceutical Synthesis:
ETHYL 3-METHOXYBENZOYLFORMATE is also utilized in the synthesis of pharmaceuticals and organic compounds. Its chemical properties make it a useful building block for creating various medications and other organic substances, contributing to the development of new and improved products in the pharmaceutical field.

InChI:InChI=1/C11H12O4/c1-3-15-11(13)10(12)8-5-4-6-9(7-8)14-2/h4-7H,3H2,1-2H3

Upstream product

• 10365-98-7 3-methoxyphenylboronic acid 
• 623-49-4 ethyl cyanoformate 
• 762-04-9 Diethyl phosphonate 
• 32025-65-3 3-methoxyphenylglyoxal 
• 27834-99-7 ethyl (3-methoxybenzoyl)acetate 
• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 64-17-5 ethanol 
• 58316-11-3 3-(dimethylamino)-1-(3-methoxyphenyl)prop-2-en-1-one 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 125532-68-5 ethyl 2-(3-methoxyphenyl)acetimidate hydrochloride 
• 1426237-48-0 ethyl 2-(3-methoxyphenyl)-2-nitroacetate 
• 2398-37-0 3-methoxyphenyl bromide 
• 95-92-1 oxalic acid diethyl ester 
• 5000-65-7 2-bromo-3'-methoxyacetophenone 

Downstream Products

• 1068161-67-0 C₁₇H₁₈N₂O₄ 
• 1220306-95-5 C₁₄H₁₅NO₄ 
• 1339804-59-9 (Z)-ethyl 2-(methoxyimino)-2-(3-methoxyphenyl)acetate 
• 1339804-79-3 (Z)-ethyl 2-(2-acetoxy-5-methoxyphenyl)-2-(methoxyimino)acetate 
• 1339804-98-6 (Z)-2-(2-ethoxy-1-(methoxyimino)-2-oxoethyl)-4-methoxyphenyl pivalate 
• 1339804-74-8 C₁₃H₁₇NO₅ 
• 1429317-21-4 (R)-tert-butyl 3-(2-ethoxy-1-hydroxy-1(3-methoxyphenyl)-2-oxoethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 1308252-53-0 tert-butyl 2-(3-methoxyphenyl)-2-oxoacetate 
• 26767-10-2 2-(3-methoxyphenyl)glyoxylic acid 

Relevant academic research and scientific papers

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.

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

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.

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.

Copper-catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates: Synthesis of aryl/heteroaryl α-keto esters

A copper catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates is described for the first time. This transformation represents a new route to synthesize α-keto esters, which are important intermediates for pharmaceuticals and organic synthesis. The reaction proceeds via in situ generation of a thionium ion that undergoes hydrolysis to furnish α-keto esters in synthetically viable yields (up to 82%).

Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds

A highly enantioselective hydrosilylation of 1,2-dicarbonyl compounds was successfully realized for the first time utilizing the combination of tricyclohexylphosphine and chiral alkenylborane derived in situ from diyne as a frustrated Lewis pair catalyst. A variety of optically active α-hydroxy ketones and esters were obtained in 52-98% yields with 86-99% ee's.

2-Oxo promoted hydrophosphonylation & aerobic intramolecular nucleophilic displacement reaction

Highly efficient catalyst free methods for the synthesis of α-hydroxy-β-oxophosphonates and α-oxoesters have been described. The existence of a 2-oxo group in α-oxoaldehydes is a key factor in promoting the reaction of the tervalent phosphite form towards 2-oxoaldehydes in the synthesis of α-hydroxy-β-oxophosphonates. The in situ activated α-C-H atom of α-hydroxy-β-oxophosphonates sustains aerobic intramolecular nucleophilic displacement in a curious way to produce α-oxoester.