2-Hexynoic acid, 4-hydroxy-6-phenyl-, ethyl ester

Base Information

• Chemical Name: 2-Hexynoic acid, 4-hydroxy-6-phenyl-, ethyl ester
• CAS No.: 128114-09-0
• Molecular Formula: C14H16O3
• Molecular Weight: 232.279
• DSSTox Substance ID: DTXSID90434552
• Nikkaji Number: J344.313B
• Mol file: 128114-09-0.mol

Synonyms:2-Hexynoic acid, 4-hydroxy-6-phenyl-, ethyl ester;128114-09-0;DTXSID90434552;4-Hydroxy-6-phenyl-2-hexynoic acid ethyl ester

Chemical Property of 2-Hexynoic acid, 4-hydroxy-6-phenyl-, ethyl ester

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 232.109944368
• Heavy Atom Count: 17
• Complexity: 291

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C#CC(CCC1=CC=CC=C1)O

Technology Process of 2-Hexynoic acid, 4-hydroxy-6-phenyl-, ethyl ester

There total 1 articles about 2-Hexynoic acid, 4-hydroxy-6-phenyl-, 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:

3-phenyl-propionaldehyde (104-53-0) + propynoic acid ethyl ester (623-47-2) → 4-Hydroxy-6-phenyl-hex-2-ynoic acid ethyl ester (128114-09-0)

Guidance literature:

With lithium diisopropyl amide; Multistep reaction; 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, -78 deg C, 30 min;

DOI:10.1021/jo00057a013

Reference yield: 65.0%

chloro-trimethyl-silane (75-77-4) + bis(2-carboethoxyethyl)zinc (911641-23-1) + 4-Hydroxy-6-phenyl-hex-2-ynoic acid ethyl ester (128114-09-0) → 5-Oxo-2-(3-phenyl-1-trimethylsilanyloxy-propyl)-cyclopent-1-enecarboxylic acid ethyl ester (128114-20-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; In diethyl ether; 1.) 0 deg C, 2.) 25 deg C;

DOI:10.1021/jo00301a003

Reference yield:

[(1-Ethoxycyclopropyl)oxy]trimethylsilane (27374-25-0) + 4-Hydroxy-6-phenyl-hex-2-ynoic acid ethyl ester (128114-09-0) → 5-Oxo-2-(3-phenyl-1-trimethylsilanyloxy-propyl)-cyclopent-1-enecarboxylic acid ethyl ester (128114-20-5)

Guidance literature:

With zinc(II) chloride; copper(I) bromide dimethylsulfide complex; Yield given. Multistep reaction; 1.a) diethyl ether, sonication, 40 min, b) r.t., 10 min, 2.a) THF, HMPA, 0 deg C, 5 min, b) to r.t., 4 h;

DOI:10.1021/jo00057a013

upstream raw materials:

3-phenyl-propionaldehyde

propynoic acid ethyl ester

Downstream raw materials:

5-Oxo-2-(3-phenyl-1-trimethylsilanyloxy-propyl)-cyclopent-1-enecarboxylic acid ethyl ester

Refernces