Methyl 6-hydroxyhex-2-ynoate

Base Information

• Chemical Name: Methyl 6-hydroxyhex-2-ynoate
• CAS No.: 123368-72-9
• Molecular Formula: C7H10 O3
• Molecular Weight: 142.155
• DSSTox Substance ID: DTXSID20473393
• Wikidata: Q82302759
• Mol file: 123368-72-9.mol

Synonyms:Methyl 6-hydroxyhex-2-ynoate;123368-72-9;METHYL 6-HYDROXY-2-HEXYNOATE;METHYL6-HYDROXY-2-HEXYNOATE;DTXSID20473393;AKOS006276629;FT-0693576

Chemical Property of Methyl 6-hydroxyhex-2-ynoate

Chemical Property:

• PSA: 46.53000
• LogP: -0.06470
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

97% ^*data from raw suppliers

METHYL 6-HYDROXY-2-HEXYNOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C#CCCCO

Technology Process of Methyl 6-hydroxyhex-2-ynoate

There total 9 articles about Methyl 6-hydroxyhex-2-ynoate 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%

6-(tetrahydro-pyran-2-yloxy)-hex-2-ynoic acid methyl ester (104803-57-8) → 6-hydroxy-hex-2-ynoic acid methyl ester (123368-72-9)

Guidance literature:

toluene-4-sulfonic acid; In methanol; at 20 ℃;

DOI:10.1021/jo0110146

Reference yield: 91.0%

Methyl 6-(tert-butyldiphenylsiloxy)-2-hexynoate (158478-17-2) → 6-hydroxy-hex-2-ynoic acid methyl ester (123368-72-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1016/j.bmc.2008.04.070

Reference yield:

1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5) → 6-hydroxy-hex-2-ynoic acid methyl ester (123368-72-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 2.5 h / -78 °C

1.2: 99 percent / tetrahydrofuran / -35 - 20 °C

2.1: 99 percent / 4-methylbenzenesulfonic acid / methanol / 20 °C

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

DOI:10.1021/jo0110146

upstream raw materials:

methanol

6-hydroxyhex-2-ynoic acid

6-(tetrahydro-pyran-2-yloxy)-hex-2-ynoic acid methyl ester

diazomethane

Downstream raw materials:

C₁₅H₁₄O₃

6-amino-9-(5-methoxycarbonylpent-4-ynyl)-8-(3,4,5-trimethoxybenzyl)-9H-purine

bis(diphenylmethyl) 2'-(5-(methoxycarbonyl)-4-pentynyl)homophthalate

2'-(5-(methoxycarbonyl)-4-pentynyl)homophthalic acid