1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne

Base Information

• Chemical Name: 1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne
• CAS No.: 1551325-45-1
• Molecular Formula: C₂₄H₂₆O₆
• Molecular Weight: 410.467
• Mol file: 1551325-45-1.mol

Synonyms:1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne

Chemical Property of 1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne

There total 6 articles about 1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne 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: 17.0%

2-methyl-4-(3,4,6-trimethoxy-2-methylphenyl)but-3-yne-2-ol (1551325-36-0) → 1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne (1551325-45-1)

Guidance literature:

2-methyl-4-(3,4,6-trimethoxy-2-methylphenyl)but-3-yne-2-ol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h; Inert atmosphere;

With dimethylglyoxal; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c3ob42333f

Reference yield:

2,4-dimethoxy-6-methyl-benzaldehyde (7149-90-8) → 1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne (1551325-45-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dihydrogen peroxide; sulfuric acid / methanol; water / 0.33 h / 0 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Inert atmosphere; Darkness

3.1: N-iodo-succinimide; trifluoroacetic acid / acetonitrile / 0.5 h / Inert atmosphere; Darkness

4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / dimethyl sulfoxide / 24 h / 70 °C / Inert atmosphere; Sealed tube

5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

5.2: 24 h / -78 - 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; copper(l) iodide; n-butyllithium; sulfuric acid; dihydrogen peroxide; potassium carbonate; diethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 4.1: |Sonogashira Cross-Coupling;

DOI:10.1039/c3ob42333f

Reference yield:

1,3-dimethoxy-5-methylbenzene (4179-19-5) → 1,4-bis(3,4,6-trimethoxy-2-methylphenyl)buta-1,3-diyne (1551325-45-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: trichlorophosphate / 24 h / 0 - 20 °C

2.1: dihydrogen peroxide; sulfuric acid / methanol; water / 0.33 h / 0 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Inert atmosphere; Darkness

4.1: N-iodo-succinimide; trifluoroacetic acid / acetonitrile / 0.5 h / Inert atmosphere; Darkness

5.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / dimethyl sulfoxide / 24 h / 70 °C / Inert atmosphere; Sealed tube

6.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

6.2: 24 h / -78 - 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; copper(l) iodide; n-butyllithium; sulfuric acid; dihydrogen peroxide; potassium carbonate; diethylamine; trifluoroacetic acid; trichlorophosphate; In tetrahydrofuran; methanol; hexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 1.1: |Vilsmeier-Haack Formylation / 5.1: |Sonogashira Cross-Coupling;

DOI:10.1039/c3ob42333f

upstream raw materials:

2-methyl-4-(3,4,6-trimethoxy-2-methylphenyl)but-3-yne-2-ol

1,3-dimethoxy-5-methylbenzene

2,4-dimethoxy-6-methyl-benzaldehyde

2,4-dimethoxyl-6-methylphenol