Benzoic acid, 3,5-diethynyl-, 2-[2-(2-methoxyethoxy)ethoxy]ethyl ester

Base Information

• Chemical Name: Benzoic acid, 3,5-diethynyl-, 2-[2-(2-methoxyethoxy)ethoxy]ethyl ester
• CAS No.: 398119-23-8
• Molecular Formula: C18H20O5
• Molecular Weight: 316.354
• Mol file: 398119-23-8.mol

Synonyms:

Chemical Property of Benzoic acid, 3,5-diethynyl-, 2-[2-(2-methoxyethoxy)ethoxy]ethyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid, 3,5-diethynyl-, 2-[2-(2-methoxyethoxy)ethoxy]ethyl ester

There total 11 articles about Benzoic acid, 3,5-diethynyl-, 2-[2-(2-methoxyethoxy)ethoxy]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: 98.0%

2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-bis[2-(1,1,1-trimethylsilyl)-1-ethynyl]benzoate (398119-22-7) → 2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-biethynylbenzoate (398119-23-8)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 0.0166667h;

DOI:10.1021/jo010918o

Reference yield: 90.0%

3,5-diethynyl-benzoic acid (883106-26-1) + triethylene glucol monomethyl ether (112-35-6,95507-80-5) → 2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-biethynylbenzoate (398119-23-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In 1,2-dichloro-ethane; at 20 ℃; for 4h;

DOI:10.1021/ja012458m

Reference yield:

triethylene glucol monomethyl ether (112-35-6,95507-80-5) → 2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-biethynylbenzoate (398119-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / diphenylammonium triflate / toluene / 18 h / Heating

2: 98 percent / Pd₂(dba)3; CuI; PPh₃ / triethylamine

3: 89 percent / tetrabutylammonium fluoride; glacial acetic acid / tetrahydrofuran / 0.08 h / 20 °C

With copper(l) iodide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diphenylammonium trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; toluene; 2: Sonogashira's coupling;

DOI:10.1021/ja046531v

upstream raw materials:

2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-bis[2-(1,1,1-trimethylsilyl)-1-ethynyl]benzoate

3,5-diethynyl-benzoic acid

triethylene glucol monomethyl ether

3-bromo-5-iodo-benzoic acid

Downstream raw materials:

C₄₆H₅₄N₂O₁₅H₄

2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-di(benzoylbiphenylethynyl)benzoate

C₄₆H₅₄N₂O₁₉

C₄₈H₅₆O₁₇

Refernces

• 1、 Zhang, Wei,Moore, Jeffrey S.. "Arylene ethynylene macrocycles prepared by precipitation-driven alkyne metathesis". . p. 12796 - 12796. Retrieved 2007/10/03.
• 2、 Zhao, Dahui,Moore, Jeffrey S.. "Synthesis and self-association of an imine-containing m-phenylene ethynylene macrocycle". . p. 3548 - 3554. Retrieved 2007/10/03.