(E)-Ethyl 3-(4-hydroxyphenyl)acrylate

Base Information

• Chemical Name: (E)-Ethyl 3-(4-hydroxyphenyl)acrylate
• CAS No.: 7362-39-2
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.214
• Hs Code.: 2918290090
• NSC Number: 408777
• DSSTox Substance ID: DTXSID501341775
• Nikkaji Number: J721.912A,J729.900A
• Pharos Ligand ID: 8MX88XDU6UW5
• Metabolomics Workbench ID: 126753
• ChEMBL ID: CHEMBL2074640
• Mol file: 7362-39-2.mol

Synonyms:ethyl coumarate

Chemical Property of (E)-Ethyl 3-(4-hydroxyphenyl)acrylate

Chemical Property:

• PSA: 46.53000
• LogP: 1.96850
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 203

Purity/Quality:

99%, ^*data from raw suppliers

(E)-Ethyl3-(4-hydroxyphenyl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=C(C=C1)O
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC=C(C=C1)O

Technology Process of (E)-Ethyl 3-(4-hydroxyphenyl)acrylate

There total 44 articles about (E)-Ethyl 3-(4-hydroxyphenyl)acrylate 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: 100.0%

ethanol (64-17-5) + p-Coumaric Acid (7400-08-0,50940-26-6) → ethyl (E)-4-hydroxycinnamate (2979-06-8,7361-92-4,7362-39-2)

Guidance literature:

With sulfuric acid; at 60 ℃;

DOI:10.1016/0957-4166(96)00377-1

Reference yield: 100.0%

(E)-ethyl 3-(4-(allyloxy)phenyl)acrylate (227097-01-0) → ethyl (E)-4-hydroxycinnamate (2979-06-8,7361-92-4,7362-39-2)

Guidance literature:

With sodium acetate; nickel; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jo9824706

Reference yield: 97.0%

ethanol (64-17-5) + para-coumaric acid (7400-08-0,50940-26-6) → ethyl 3-(4-hydroxyphenyl)prop-2-enoate (7361-92-4,7362-39-2,2979-06-8)

Guidance literature:

With acetyl chloride; at 20 ℃; for 30h; Inert atmosphere;

DOI:10.1021/jacs.8b13506

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

4-hydroxy-benzaldehyde

ethanol

ethyl bromoacetate

Downstream raw materials:

para-coumaric acid

3-(4-acetoxyphenyl)acrylic acid

2,3-dibromo-3-(4-acetoxyphenyl)propionic acid ethyl ester

3-(4-hydroxyphenyl)prop-2-yn-1-oic acid

Refernces

• 1、 Balmas, Virgilio,Carta, Paola,Casalini, Stefano,Chtioui, Wiem,Delogu, Giovanna,Dettori, Maria A.,Fabbri, Davide,Migheli, Quirico,Oufensou, Safa. "Prenylated trans-cinnamic esters and ethers against clinical fusarium spp.: Repositioning of natural compounds in antimicrobial discovery". . . Retrieved 2021/06/14.
• 2、 Kashid, Abhijit A.,Patil, Dharmaraj J.,Mali, Ramling D.,Patil, Vijay P.,Neethu,Meroliya, Heena K.,Waghmode, Shobha A.,Iyer, Suresh. "Bimetallic Ni–Pd Synergism—Mixed Metal Catalysis of the Mizoroki-Heck Reaction and the Suzuki–Miyaura Coupling of Aryl Bromides". . p. 353 - 358. Retrieved 2020/08/05.