BENZENEPROPANOIC ACID, 4-CARBOXY-, A-ETHYL ESTER

Base Information

• Chemical Name: BENZENEPROPANOIC ACID, 4-CARBOXY-, A-ETHYL ESTER
• CAS No.: 267888-21-1
• Molecular Formula: C12H14 O4
• Molecular Weight: 222.241
• Mol file: 267888-21-1.mol

Synonyms:Benzenepropanoicacid, 4-carboxy-, a-ethyl ester (9CI); 4-(2-Ethoxycarbonylethyl)benzoic acid

Chemical Property of BENZENEPROPANOIC ACID, 4-CARBOXY-, A-ETHYL ESTER

Chemical Property:

• Boiling Point: 358.3±25.0 °C(Predicted)
• PKA: 4.29±0.10(Predicted)
• PSA: 63.60000
• Density: 1.183±0.06 g/cm3(Predicted)
• LogP: 1.88050

Purity/Quality:

99% ^*data from raw suppliers

4-(3-Ethoxy-3-oxopropyl)benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BENZENEPROPANOIC ACID, 4-CARBOXY-, A-ETHYL ESTER

There total 3 articles about BENZENEPROPANOIC ACID, 4-CARBOXY-, A-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: 96.0%

ethyl (E)-3-[4-(hydroxycarbonyl)phenyl]prop-2-enoate (91047-75-5) → 4-(3-ethoxy-3-oxopropyl)benzoic acid (267888-21-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; ethyl acetate; at 25 ℃; for 48h; under 2844.39 Torr;

DOI:10.1016/j.bmcl.2017.09.056

Reference yield:

benzoic acid tert-butyl ester (774-65-2) + ethyl acrylate (140-88-5,9003-32-1) → 3-(2-ethoxycarbonylethyl)benzoic acid (874204-67-8) + 4-(3-ethoxy-3-oxopropyl)benzoic acid (267888-21-1)

Guidance literature:

benzoic acid tert-butyl ester; ethyl acrylate; With 2,6-di(2-ethylhexyl)pyridine; oxygen; palladium diacetate; acetic anhydride; at 20 - 90 ℃;

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 12h;

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; regioselective reaction;

Reference yield:

4-Carboxybenzaldehyde (619-66-9) → 4-(3-ethoxy-3-oxopropyl)benzoic acid (267888-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 4 h / Reflux

2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 48 h / 25 °C / 2844.39 Torr

With palladium 10% on activated carbon; hydrogen; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/j.bmcl.2017.09.056

upstream raw materials:

benzoic acid tert-butyl ester

ethyl acrylate

4-Carboxybenzaldehyde

ethyl (E)-3-[4-(hydroxycarbonyl)phenyl]prop-2-enoate

Downstream raw materials:

3-(4-chlorocarbonyl-phenyl)propionic acid ethyl ester

Refernces

• 1、 Zhang, Yang-Hui,Shi, Bing-Feng,Yu, Jin-Quan. "Pd(II)-Catalyzed olefination of electron-deficient arenes using 2,6-dialkylpyridine ligands". supporting information; experimental part. p. 5072 - 5074. Retrieved 2009/09/30.