3-(3-METHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

Base Information

• Chemical Name: 3-(3-METHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
• CAS No.: 27834-99-7
• Molecular Formula: C12H14 O4
• Molecular Weight: 222.241
• Hs Code.: 2918990090
• European Community (EC) Number: 673-420-0
• DSSTox Substance ID: DTXSID90374883
• Nikkaji Number: J184.137H
• Wikidata: Q82163458
• Mol file: 27834-99-7.mol

Synonyms:Aceticacid, m-anisoyl-, ethyl ester (8CI); 3-(3-Methoxyphenyl)-3-oxo-propionic acidethyl ester; 3-(3-Methoxyphenyl)-3-oxopropanoic acid ethyl ester; Ethyl(3-methoxybenzoyl)acetate; Ethyl (m-methoxybenzoyl)acetate; Ethyl2-(3-methoxybenzoyl)acetate; Ethyl 3-(3-methoxyphenyl)-3-oxopropanoate; Ethyl3-anisoylacetate; Ethyl m-anisoylacetate

Chemical Property of 3-(3-METHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

Chemical Property:

• Vapor Pressure: 0.000787mmHg at 25°C
• Refractive Index: n20/D 1.5360(lit.)
• Boiling Point: >268 °C(lit.)
• PKA: 10.28±0.46(Predicted)
• Flash Point: >230 °F
• PSA: 52.60000
• Density: 1.146 g/mL at 25 °C(lit.)
• LogP: 1.83110
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 222.08920892
• Heavy Atom Count: 16
• Complexity: 249

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl3-(3-Methoxyphenyl)-3-oxopropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C1=CC(=CC=C1)OC
• Uses: Reactant involved in:? ;Stereoselective ketonization-olefination of indoles1? ;Lewis base catalyzed hydrosilylation2 and sequential reactions3,4? ;Asymmetric hydrogenation5? ;Organocatalytic reduction by trichlorosilane6 Reactant involved in:Stereoselective ketonization-olefination of indolesLewis base catalyzed hydrosilylation and sequential reactionsAsymmetric hydrogenationOrganocatalytic reduction by trichlorosilane

Technology Process of 3-(3-METHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

There total 15 articles about 3-(3-METHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER 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: 95.0%

3-methoxy-N-phenylbenzamide (6833-23-4) + ethyl acetate (141-78-6) → ethyl (3-methoxybenzoyl)acetate (27834-99-7)

Guidance literature:

3-methoxy-N-phenylbenzamide; With dmap; di-tert-butyl dicarbonate;

ethyl acetate; With lithium hexamethyldisilazane;

DOI:10.1021/acs.joc.0c02868

Reference yield: 82.0%

dicobalt octacarbonyl (15226-74-1,61091-28-9,61117-58-6) + 3-methoxy-1-iodobenzene (766-85-8) + ethyl potassium malonate (6148-64-7) → ethyl (3-methoxybenzoyl)acetate (27834-99-7)

Guidance literature:

With 1H-imidazole; palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride; In tetrahydrofuran; at 90 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.tetlet.2014.04.087

Reference yield: 81.0%

3-methoxy-N-phenyl-N-tosylbenzamide + ethyl acetate (141-78-6) → ethyl (3-methoxybenzoyl)acetate (27834-99-7)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 25 ℃; for 2h; chemoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1021/acs.joc.0c02868

upstream raw materials:

ethyl acetoacetate

m-anisoyl chloride

methyl 3-methoxybenzoate

ethyl acetate

Downstream raw materials:

6-(3-methoxy-phenyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

3-(3-methoxyphenyl)propanoic acid ethyl ester

(E)-3-(3-Methoxy-phenyl)-3-(2-oxo-2,3-dihydro-indol-1-ylamino)-acrylic acid ethyl ester

3-(m-methoxyphenyl)-3-(1H-indol-4-ylamino)acrylic acid ethyl ester

Refernces

• 1、 Chen, Jiajia,Joseph, Devaneyan,Xia, Yuanzhi,Lee, Sunwoo. "Amide/Ester Cross-Coupling via C-N/C-H Bond Cleavage: Synthesis of β-Ketoesters". . p. 5943 - 5953. Retrieved 2021/04/02.
• 2、 Tu, Jia-Lin,Liu, Jia-Li,Tang, Wan,Su, Ma,Liu, Feng. "Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis". supporting information. p. 1222 - 1226. Retrieved 2020/02/15.