3-Ethoxy-3-oxo-2-phenylpropanoic acid

Base Information

• Chemical Name: 3-Ethoxy-3-oxo-2-phenylpropanoic acid
• CAS No.: 17097-90-4
• Molecular Formula: C11H12 O4
• Molecular Weight: 208.214
• Hs Code.: 2918990090
• European Community (EC) Number: 832-618-9
• DSSTox Substance ID: DTXSID90369618
• Nikkaji Number: J1.394.223D
• Mol file: 17097-90-4.mol

Synonyms:3-ethoxy-3-oxo-2-phenylpropanoic acid;17097-90-4;2-Phenyl-malonic acid monoethyl ester;Maybridge3_005541;ethyl hydrogen phenylmalonate;Oprea1_116521;phenyl malonic acid ethyl ester;SCHEMBL1275691;phenyl(ethoxycarbonyl)acetic acid;AMY3867;DTXSID90369618;INQWZSLKTMTMSK-UHFFFAOYSA-N;HMS1446L19;2-Phenylmalonic acid 1-ethyl ester;2-Phenylmalonic acid monoethyl ester;MFCD00091621;3-ethoxy-3-oxo-2-phenylpropanoicacid;AKOS022181874;IDI1_016928;3-ethoxy-3-oxo-2-phenyl-propionic acid;CS-0239775;FT-0734331;EN300-218800;Z1508916165

Chemical Property of 3-Ethoxy-3-oxo-2-phenylpropanoic acid

Chemical Property:

• Melting Point: 76-77 °C(Solv: dichloromethane (75-09-2))
• Boiling Point: 153-155 °C(Press: 0.2 Torr)
• PKA: 3.07±0.10(Predicted)
• PSA: 63.60000
• Density: 1.432 g/cm3(Temp: 22 °C)
• LogP: 1.41790
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

3-ethoxy-3-oxo-2-phenylpropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C1=CC=CC=C1)C(=O)O

Technology Process of 3-Ethoxy-3-oxo-2-phenylpropanoic acid

There total 7 articles about 3-Ethoxy-3-oxo-2-phenylpropanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

carbon dioxide (124-38-9,18923-20-1) + Ethyl 2-phenylethanoate (101-97-3) → 2-phenylmalonic acid monoethyl ester (17097-90-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -60 - 20 ℃;

DOI:10.1021/ol063074+

Reference yield: 94.0%

diethyl 2-phenylmalonate (83-13-6) → 2-phenylmalonic acid monoethyl ester (17097-90-4)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1016/j.tetlet.2008.05.007

Reference yield: 65.0%

2.2-dimethyl-5-phenyl-1,3-dioxane-4,6-dione (15231-78-4) → 2-phenylmalonic acid monoethyl ester (17097-90-4)

Guidance literature:

In toluene; at 80 ℃; for 8h;

DOI:10.3762/bjoc.17.135

upstream raw materials:

diethyl 2-phenylmalonate

phenylacetic acid

chloroformic acid ethyl ester

carbon dioxide

Downstream raw materials:

3-oxo-2-phenyl-adipic acid diethyl ester

ethyl α,α-bis(methylthio)phenylacetate

α-deuterio(phenyl)acetic acid

Ethyl 2-phenylethanoate

Refernces

• 1、 Volonterio, Alessandro,Zanda, Matteo. "Three-component, one-pot sequential synthesis of N-Aryl, N′-alkyl barbiturates". . p. 841 - 844. Retrieved 2007.
• 2、 Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania. "Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)". . p. 2085 - 2094. Retrieved 2021/09/02.
• 3、 Bagum, Halima,Christensen, Kirsten E.,Genov, Miroslav,Pretsch, Alexander,Pretsch, Dagmar,Moloney, Mark G.. "Synthetic access to 3,4-disubstituted pyroglutamates from tetramate derivatives from serine, allo-threonine and cysteine". . . Retrieved 2019/09/07.