(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

Base Information

• Chemical Name: (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester
• CAS No.: 222555-06-8
• Molecular Formula: C13H18O4
• Molecular Weight: 238.284
• Hs Code.: 2918990090
• European Community (EC) Number: 675-850-4
• DSSTox Substance ID: DTXSID50431204
• Nikkaji Number: J2.197.264I
• Wikidata: Q72471661
• Mol file: 222555-06-8.mol

Synonyms:222555-06-8;(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester;(S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate;ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate;(S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester;(s)-2-ethoxy-3-(4-hydroxyphenyl)propionic acid ethyl ester;(S)-Ethyl2-ethoxy-3-(4-hydroxyphenyl)propanoate;SCHEMBL977513;DTXSID50431204;NEJJCKFYYBEQRQ-LBPRGKRZSA-N;(2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester;XIA55506;MFCD06796580;AS-37399;CS-0151952;A13355;ethyl (s)-2-ethoxyl-3-p-hydroxyphenylpropionate;(S)-ethyl-2-ethoxy-3-(4-hydroxyphenyl)propanoate;Ethyl (2S)-ethoxy-3-(4-hydroxyphenyl)-propanoate;ethyl (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate;ethyl 2(S)-ethoxy-3-(4-hydroxyphenyl)propanoate;ethyl(2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate;Ethyl(2S)-3-(4-hydroxyphenyl)-2-ethoxypropanoate;(S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate;ethyl-(2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate;(S)-ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate;(2S)-2-ethoxy-3-(4-hydroxyphenyl)-propionic acid ethyl ester;(S)-2-ethoxy-3-(4-hydroxyphenyl) propanoic acid ethyl ester;(S)-2-ethoxy-3-(4-hydroxyphenyl)-propionic acid ethyl ester

Chemical Property of (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.515
• Boiling Point: 367.296 °C at 760 mmHg
• PKA: 9.75±0.15(Predicted)
• Flash Point: 134.932 °C
• PSA: 55.76000
• Density: 1.116g/cm³
• LogP: 1.90290
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 238.12050905
• Heavy Atom Count: 17
• Complexity: 222

Purity/Quality:

97% ^*data from raw suppliers

Ethyl(S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(CC1=CC=C(C=C1)O)C(=O)OCC
• Isomeric SMILES: CCO[C@@H](CC1=CC=C(C=C1)O)C(=O)OCC
• Uses: Ethyl (S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate, is an intermediate in the synthesis of glitazars, novel Thiophene substituted oxazole containing α-ethoxy phenylpropanoic acid derivatives, as very potent PPARα/γ dual agonist demonstrating potent antidiabetic and lipid lowering activity at a very low dose.

Technology Process of (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

There total 40 articles about (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-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: 99.0%

ethyl (2S)-3-[4-(benzyloxy)phenyl]-2-ethoxypropanoate (251454-50-9) → ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate (222555-06-8)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; for 10h; under 2844.39 Torr;

Reference yield: 95.0%

ethanol (64-17-5) + (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5) → ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate (222555-06-8)

Guidance literature:

With sulfuric acid; for 4h; enantioselective reaction; Reflux;

DOI:10.1016/j.tetlet.2016.06.093

Reference yield:

(S)-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoic acid (162919-37-1) → ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate (222555-06-8)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄

2: imidazole / dimethylformamide / 18 h / 25 °C

3: CH₃COH; Et₃SiH; BiBr₃ / acetonitrile / 25 °C

4: H₂ / Pd/C / ethanol / 20 °C / 2585.74 Torr

With 1H-imidazole; triethylsilane; bismuth(III) bromide; sulfuric acid; hydrogen; acetaldehyde; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo050268e

upstream raw materials:

ethyl (2S)-3-[4-(benzyloxy)phenyl]-2-ethoxypropanoate

(2S)-3-[4-(benzyloxy)phenyl]-2-ethoxypropanoic acid

ethanol

3-(4-benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

Downstream raw materials:

(2S)-3-[4-(3,3-Diphenyl-allyloxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

(2S)-3-[4-(3,3-Di-p-tolyl-allyloxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

(E)-(S)-3-{4-[3-(3,5-bis-cyclopentyloxy-phenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester

(E)-(S)-3-{4-[3-(3,5-bis-benzyloxy-phenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester