Production Method 1

5764-85-2

94-02-0

Reaction Conditions

1.1 Reagents: Manganese oxide (MnO2) (electrolytic) Solvents: Hexane

Reference

Oxidation of alcohols with electrolytic manganese dioxide. Its application for the synthesis of insect pheromones

Tsuboi, Sadao; Ishii, Naomi; Sakai, Takashi; Tari, Isao; Utaka, Masanori, Bulletin of the Chemical Society of Japan, 1990, 63(7), 1888-93

Production Method 2

2216-94-6

94-02-0

Reaction Conditions

1.1 Reagents: 4-Methylbenzaldehyde oxime Solvents: Dimethylformamide ;  3 h, 100 °C

Reference

Base-Promoted Difunctionalization of Alkynes: One-Pot Synthesis of Polysubstituted Chromones+

Wang, Mengdan ; Cheng, Lu; Ma, Junying; Lu, Weiwei; Wang, Junling, European Journal of Organic Chemistry, 2023, 26(32),

Production Method 3

98-86-2

94-02-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  overnight, 70 °C; 70 °C → rt
1.2 Solvents: Water ;  cooled

Reference

The construction of chiral 3-acyl bicyclolactams via a RuPHOX/Pd catalyzed asymmetric allylic substitution cascade of α-carbonylamides

Dong, Siqi; Xu, Shaofeng; Zou, Yashi; Li, Zhaodi; Xu, Kai; et al, Organic Chemistry Frontiers, 2023, 10(7), 1731-1737

Production Method 4

6148-64-7

98-88-4

94-02-0

Reaction Conditions

1.1 Reagents: Triethylamine ,  Magnesium chloride Solvents: Acetonitrile
1.2 -

Reference

A safe, economical method for the preparation of β-oxo esters

Clay, Ronald J.; Collom, Thomas A.; Karrick, Gregory L.; Wemple, James, Synthesis, 1993, (3), 290-2

Production Method 5

98-86-2

94-02-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Toluene ;  rt → 110 °C
1.2 Solvents: Toluene ;  10 - 20 min, 110 °C; 110 °C → reflux; reflux → rt
1.3 Reagents: Acetic acid ;  rt

Reference

Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines

Chen, Zhiwei ; Shi, Guang; Tang, Wei; Sun, Jie; Wang, Wenxing, European Journal of Organic Chemistry, 2021, 2021(6), 951-955

Production Method 6

54882-05-2

94-02-0

Reaction Conditions

1.1 Reagents: Potassium fluoride (aluminum oxide supported) ;  4 min

Reference

Microwave-assisted β-elimination of sulfoxides on KF/Al2O3 support under solvent-free conditions

Moghaddam, Firouz Matloubi; Baradjee, Ghasem Rezanejade, Journal of Sulfur Chemistry, 2005, 26(4-5), 325-329

Production Method 7

1028408-98-1

94-02-0

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  1 h, rt; 2 h, 50 °C

Reference

A novel synthetic method for β-keto esters

Qian, Hao; Ge, Chunrong; Huang, Xian, Journal of Chemical Research, 2007, (3), 160-161

Production Method 8

2216-94-6

94-02-0

Reaction Conditions

1.1 Catalysts: Silver triflate ,  2249872-40-8 Solvents: Methanol ;  18.5 h, 40 °C

Reference

Hydroalkoxylation of terminal and internal alkynes catalyzed by dinuclear gold(I) complexes with bridging Di(N-heterocyclic carbene) ligands

Marcheggiani, Elena; Tubaro, Cristina ; Biffis, Andrea; Graiff, Claudia ; Baron, Marco, Catalysts, 2020, 10(1),

Production Method 9

614-20-0

94-02-0

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Ethanol ;  15 h, reflux

Reference

Catalytic reductive deoxygenation of esters to ethers driven by hydrosilane activation through non-covalent interactions with a fluorinated borate salt

Rysak, Vincent; Dixit, Ruchi; Trivelli, Xavier; Merle, Nicolas; Agbossou-Niedercorn, Francine; et al, Catalysis Science & Technology, 2020, 10(14), 4586-4592

Production Method 10

141-97-9

98-88-4

94-02-0

Reaction Conditions

1.1 Reagents: Calcium oxide Solvents: Chloroform ;  10 min, < 5 °C
1.2 2 h, < 5 °C; 40 °C; 6 h, 40 °C
1.3 Catalysts: Sodium hydroxide ;  40 °C → 62 °C; 4 h, 62 °C

Reference

Method for preparing ethyl benzoyl acetate

, China, , ,

Production Method 11

5908-41-8

94-02-0

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -78 °C; 30 min, -78 °C
1.2 Reagents: Methanol ;  -78 °C → 0 °C

Reference

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters

Galliford, Chris V.; Scheidt, Karl A., Chemical Communications (Cambridge, 2008, (16), 1926-1928

Production Method 12

27262-59-5

94-02-0

Reaction Conditions

1.1 Catalysts: Dichlorobis(triphenylphosphine)palladium ;  5 h, rt

Reference

tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions

Chen, Shufeng; Yuan, Fang; Zhao, Haiying; Li, Baoguo, RSC Advances, 2013, 3(31), 12616-12620

Production Method 13

6148-64-7

65-85-0

94-02-0

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  2 h, 25 °C
1.2 Reagents: 1,1′-Carbonyldiimidazole ,  Magnesium chloride Solvents: Tetrahydrofuran ;  2 h, 25 °C
1.3 25 °C
1.4 Reagents: Hydrochloric acid Solvents: Water ;  25 °C

Reference

Development and application of a solution-phase automated synthesizer, 'ChemKonzert'

Machida, Kazuhiro; Hirose, Yoichiro; Fuse, Shinichiro; Sugawara, Tohru; Takahashi, Takashi, Chemical & Pharmaceutical Bulletin, 2010, 58(1), 87-93

Production Method 14

6148-64-7

10364-94-0

94-02-0

Reaction Conditions

1.1 Reagents: Chlorotrimethylsilane ,  1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetonitrile
1.2 Solvents: Tetrahydrofuran

Reference

A process for the synthesis of β-keto esters using in-situ generated trimethylsilyl malonates

Wang, Xui; Monte, William T.; Napier, James J.; Ghannam, Aneen, Tetrahedron Letters, 1994, 35(50), 9323-6

Production Method 15

98-86-2

94-02-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Toluene ;  rt → reflux; 1 - 2 h, reflux; 15 - 20 min, reflux; reflux → rt
1.2 Reagents: Acetic acid ;  rt; rt

Reference

Deoxygenation of oximes for the synthesis of pyrrolines via hydroimination cyclization

Han, Wencheng; Liu, Wen-Deng; Su, Junqi; Zhao, Jiannan, Organic & Biomolecular Chemistry, 2023, 21(16), 3350-3354

Production Method 16

98-86-2

94-02-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  30 min, rt; 15 - 20 min, rt → reflux; 2 - 3 h, reflux

Reference

Iridium(III)-catalyzed C(3)-H Alkylation of Isoquinolines via Metal Carbene Migratory Insertion

Jha, Neha; Singh, Roushan Prakash; Saxena, Paridhi; Kapur, Manmohan, Organic Letters, 2021, 23(22), 8694-8698

Production Method 17

98-86-2

94-02-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Toluene ;  1 - 2 h, reflux; 15 - 20 min, reflux; reflux → rt
1.2 Reagents: Acetic acid ;  rt

Reference

Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β'-Keto-β-Amino Esters via Dynamic Kinetic Resolution

Ling, Fei ; Wang, Yifan; Huang, An; Wang, Ze; Wang, Shiliang; et al, Advanced Synthesis & Catalysis, 2021, 363(20), 4714-4719

Production Method 18

98-86-2

94-02-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  rt → reflux
1.2 Solvents: Tetrahydrofuran ;  rt; overnight, rt
1.3 Reagents: Acetic acid Solvents: Water ;  cooled

Reference

Preparing method and application of pyrazoloquinoline derivative

, China, , ,

Production Method 19

98-86-2

94-02-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Toluene ;  1 - 2 h, reflux; 15 - 20 min, reflux; reflux → rt
1.2 Reagents: Acetic acid ;  rt
1.3 Reagents: Water ;  cooled

Reference

Highly Diastereoselective and Enantioselective Synthesis of α-Hydroxy β-Amino Acid Derivatives: Lewis Base Catalyzed Hydrosilylation of α-Acetoxy β-Enamino Esters

Jiang, Yan; Chen, Xing; Zheng, Yongsheng; Xue, Zhouyang; Shu, Chang; et al, Angewandte Chemie, 2011, 50(32), 7304-7307

Production Method 20

100-52-7

94-02-0

Reaction Conditions

1.1 Catalysts: Tungstate(3-), tetracosa-μ-oxododecaoxo[μ12-[phosphato(3-)-κO:κO:κO:κO′:κO′:κO′:… Solvents: Dichloromethane ;  2.0 h, rt

Reference

The silver salt of 12-tungstophosphoric acid. A mild and selective catalyst for the synthesis of β-ketoesters via C-H insertion

Yadav, J. S.; Reddy, B. V. Subba; Purnima, K. V.; Jhansi, S.; Nagaiah, K.; et al, Catalysis Communications, 2008, 9(14), 2361-2364

Ethyl benzoylacetate Raw materials

• Ethyl acetoacetate
• Ethyl potassium malonate
• Phenyl(trimethylsilyl)methanone
• Benzoic acid
• Ethyl β-hydroxy-α-(phenylsulfinyl)benzenepropanoate
• N-Benzoylimidazole
• Ethyl 3-hydroxy-3-phenylpropanoate
• 3-Oxo-3-phenylpropanoic acid
• Ethyl phenylpropiolate
• Benzoyl chloride
• Acetophenone
• Benzaldehyde
• Benzenepropanoic acid, a-diazo-b-hydroxy-, ethyl ester
• Ethyl β-hydroxy-α-(phenylseleno)benzenepropanoate

Ethyl benzoylacetate Preparation Products

• Ethyl benzoylacetate (94-02-0)

• 1. Alt-proteins: A promising future
• 2. An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening
  Chengbin Yang,Hing Lun Tsang,Pui Man Lau,Ken-Tye Yong,Ho Pui Ho,Siu Kai Kong Analyst, 2017,142, 3579-3587
• 3. An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement?
  Piotr Szcze?niak,Sebastian Stecko RSC Adv., 2015,5, 30882-30888
• 4. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
  Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin Fan J. Mater. Chem. B, 2019,7, 3088-3099
• 5. An aptamer-based keypad lock system?
  Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang Wang Chem. Commun., 2012,48, 802-804

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Ethyl benzoylacetate (CAS No. 94-02-0): A Comprehensive Overview

Ethyl benzoylacetate, with the chemical formula C₉H₁₀O₃ and the CAS number 94-02-0, is a significant compound in the field of organic chemistry and industrial applications. This ester, characterized by its pleasant floral fragrance, has garnered considerable attention due to its diverse utility in fragrances, flavors, and as an intermediate in pharmaceutical synthesis. The compound's unique structural properties make it a valuable candidate for various chemical transformations, contributing to its widespread use in multiple industries.

The synthesis of ethyl benzoylacetate typically involves the reaction between benzoylacetic acid and ethanol under acidic conditions. This process highlights the compound's role as a derivative of both benzoic acid and acetic acid, which are fundamental in organic synthesis. The esterification reaction not only underscores the versatility of ethyl benzoylacetate but also demonstrates its importance in producing more complex molecules.

In recent years, ethyl benzoylacetate has been explored for its potential applications in pharmaceutical research. Its structural motif, which includes both aromatic and aliphatic components, makes it a promising precursor for the development of novel therapeutic agents. For instance, researchers have investigated its derivatives as possible candidates for anti-inflammatory and analgesic drugs. The presence of a benzoyl group provides a scaffold that can be modified to enhance bioactivity, while the acetoxyethyl side chain offers additional functionalization possibilities.

The compound's olfactory properties have also led to its extensive use in the fragrance industry. Ethyl benzoylacetate is known for its sweet, fruity aroma, often described as resembling cherry or almond blossoms. This characteristic makes it a popular choice in perfumery and flavoring agents for food products. Its stability under various conditions further enhances its appeal, ensuring consistent quality in end products.

From an industrial perspective, ethyl benzoylacetate serves as a key intermediate in the production of other chemicals. Its reactivity allows for further functionalization through processes such as hydrolysis or transesterification, enabling the synthesis of more complex molecules. These transformations are crucial in pharmaceutical manufacturing, where intermediates like ethyl benzoylacetate play a pivotal role in constructing intricate drug molecules.

Recent advancements in green chemistry have also highlighted ethyl benzoylacetate's potential in sustainable practices. Researchers have been exploring eco-friendly synthetic routes that minimize waste and reduce energy consumption. For example, catalytic processes using biodegradable solvents have been developed to enhance the efficiency of ethyl benzoylacetate production. Such innovations align with global efforts to promote environmentally responsible chemical manufacturing.

The compound's role in material science is another area of growing interest. Ethyl benzoylacetate has been investigated for its properties as a monomer or crosslinking agent in polymer formulations. Its ability to impart specific characteristics to polymers makes it valuable in developing advanced materials with tailored properties. These materials could find applications in coatings, adhesives, and even biodegradable plastics.

In conclusion, ethyl benzoylacetate (CAS No. 94-02-0) is a multifaceted compound with significant implications across multiple industries. Its applications range from pharmaceuticals and fragrances to industrial chemistry and material science. The ongoing research into its derivatives and synthetic pathways underscores its importance as a chemical building block. As scientific understanding advances, the potential uses for ethyl benzoylacetate are likely to expand further, reinforcing its status as a cornerstone of modern chemical innovation.

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