Ethyl 3-(4-tert-butylphenyl)prop-2-enoate

Base Information

• Chemical Name: Ethyl 3-(4-tert-butylphenyl)prop-2-enoate
• CAS No.: 105393-26-8
• Molecular Formula: C15H20O2
• Molecular Weight: 232.323
• DSSTox Substance ID: DTXSID90698450
• Mol file: 105393-26-8.mol

Synonyms:Ethyl 3-(4-tert-butylphenyl)prop-2-enoate;105393-26-8;DTXSID90698450;PQOOCBARRHHHBD-UHFFFAOYSA-N;4-t-butylcinnamic acid ethyl ester

Chemical Property of Ethyl 3-(4-tert-butylphenyl)prop-2-enoate

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 232.146329876
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 3-(4-tert-butylphenyl)prop-2-enoate

There total 3 articles about Ethyl 3-(4-tert-butylphenyl)prop-2-enoate 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:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 4-tert-Butylbenzaldehyde (939-97-9) → ethyl 3-(4-t-butylphenyl) propenoate (105393-26-8)

Guidance literature:

In tetrahydrofuran; ethyl acetate; mineral oil;

Reference yield:

tert-butylbenzene (253185-03-4,253185-04-5) + ethyl acrylate (140-88-5,9003-32-1) → ethyl 3-(4-t-butylphenyl) propenoate (105393-26-8) + C15H20O2

Guidance literature:

With 3,5-bis(trifluoromethyl)pyridin-2(1H)-one; silver(I) acetate; palladium diacetate; at 100 ℃; for 24h; Overall yield = 69 %; regioselective reaction; Sealed tube;

DOI:10.1038/nature24632

Reference yield:

4-tert-Butylbenzaldehyde (939-97-9) + (carbethoxymethyl)triphenylphosphonium bromide (1530-45-6) → ethyl 3-(4-t-butylphenyl) propenoate (105393-26-8)

Guidance literature:

(carbethoxymethyl)triphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; for 0.5h; Inert atmosphere;

4-tert-Butylbenzaldehyde; In tetrahydrofuran; for 4h; Inert atmosphere;

DOI:10.1039/c9cc04006d

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

4-tert-Butylbenzaldehyde

tert-butylbenzene

ethyl acrylate

Downstream raw materials:

diethyl (2-(4-(tert-butyl)phenyl)-2-oxoethyl)phosphonate

4-tert-butyl-trans-cinnamic acid

(E)-3-(4-tert-Butyl-phenyl)-acryloyl chloride

(E)-3-(4-(tert-butyl)phenyl)prop-2-en-1-ol

Refernces

• 1、 Chen, Xiao-Yue,Wu, Yichen,Zhou, Jian,Wang, Peng,Yu, Jin-Quan. "Synthesis of β-Arylethenesulfonyl Fluoride via Pd-Catalyzed Nondirected C-H Alkenylation". . p. 1426 - 1429. Retrieved 2019.
• 2、 Yang, Bo,Wang, Zhong-Xia. "Synthesis of Allylsilanes via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Allyl Alcohols". supporting information. p. 7965 - 7969. Retrieved 2019/10/19.