Ethyl 2-(3-methylphenyl)-2-oxoacetate

Base Information

• Chemical Name: Ethyl 2-(3-methylphenyl)-2-oxoacetate
• CAS No.: 66644-68-6
• Molecular Formula: C11H12O3
• Molecular Weight: 192.214
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID40374535
• Nikkaji Number: J3.478.591K
• Wikidata: Q82163153
• Mol file: 66644-68-6.mol

Synonyms:66644-68-6;ETHYL 3-METHYLBENZOYLFORMATE;ethyl 2-(3-methylphenyl)-2-oxoacetate;Ethyl 2-oxo-2-(m-tolyl)acetate;ethyl 2-oxo-2-m-tolylacetate;3-Methyl-oxo-benzeneacetic acid ethyl ester;SCHEMBL2007367;DTXSID40374535;ETHYL3-METHYLBENZOYLFORMATE;KSCQWCKUWIRNOQ-UHFFFAOYSA-N;oxo-m-tolylacetic acid ethyl ester;ethyl 2-(m-tolyl)-2-oxo-acetate;(m-tolyl)glyoxylic acid ethyl ester;Ethyl (3-methylphenyl)(oxo)acetate;MFCD01311168;AKOS006223929;ethyl 3-methylbenzoylformate, AldrichCPR;(3-Methylphenyl)oxoacetic acid ethyl ester;CS-0298742;EN300-43486;Benzeneacetic acid,3-methyl-a-oxo-,ethyl ester;A835509

Chemical Property of Ethyl 2-(3-methylphenyl)-2-oxoacetate

Chemical Property:

• Vapor Pressure: 0.00178mmHg at 25°C
• Refractive Index: 1.512
• Boiling Point: 293 °C at 760 mmHg
• Flash Point: 129.3 °C
• PSA: 43.37000
• Density: 1.106 g/cm³
• LogP: 1.74080
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

Oxo-m-tolylaceticacidethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 2-(3-methylphenyl)-2-oxoacetate

There total 18 articles about Ethyl 2-(3-methylphenyl)-2-oxoacetate 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: 86.0%

1-chloro-3-methylbenzene (108-41-8) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-oxo-2-(m-tolyl)acetate (66644-68-6)

Guidance literature:

1-chloro-3-methylbenzene; With lithium; In diethyl ether; at 3 - 6 ℃;

With copper(l) cyanide; In tetrahydrofuran; diethyl ether; at 3 - 6 ℃; for 0.416667h; Cooling with ice;

Ethyl oxalyl chloride; In tetrahydrofuran; diethyl ether; at 3 - 20 ℃; for 1.25h;

DOI:10.1021/ol302672n

Reference yield: 83.0%

ethanol (64-17-5) + 3-(dimethylamino)-1-(3-methylphenyl)-2-propen-1-one → ethyl 2-oxo-2-(m-tolyl)acetate (66644-68-6)

Guidance literature:

With acetic acid; Rose Bengal lactone; at 20 ℃; for 24h; chemoselective reaction; Molecular sieve; Photolysis;

DOI:10.1039/c9gc01357a

Reference yield: 82.0%

meta-bromotoluene (591-17-3) + oxalic acid diethyl ester (95-92-1) → ethyl 2-oxo-2-(m-tolyl)acetate (66644-68-6)

Guidance literature:

meta-bromotoluene; With magnesium; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

oxalic acid diethyl ester; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201007568

upstream raw materials:

oxalic acid diethyl ester

m-tolylmagnesium bromide

ethanol

2-bromo-3'-methylacetophenone

Downstream raw materials:

ethyl α-hydroxy-3-methylphenylacetate

3-methylphenyloxoacetic acid

ethyl 2-hydroxy-2-m-tolylpent-4-enoate

(R)-ethyl 2-hydroxy-3-nitro-2-(3-tolyl)-propanoate

Refernces

• 1、 Li, Bowen,Aliyu, Muinat A.,Gao, Zhenhua,Li, Tiejun,Dong, Wei,Li, Junchen,Shi, Enxue,Tang, Wenjun. "General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling". supporting information. p. 4974 - 4978. Retrieved 2020/07/03.
• 2、 Ni, Ke,Meng, Ling-Guo,Ruan, Hongjie,Wang, Lei. "Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters". supporting information. p. 8438 - 8441. Retrieved 2019/07/22.