(2Z,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal

Base Information

• Chemical Name: (2Z,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal
• CAS No.: 69877-39-0
• Molecular Formula: C₁₆H₂₀O₂
• Molecular Weight: 244.334
• DSSTox Substance ID: DTXSID001160221
• Mol file: 69877-39-0.mol

Synonyms:DTXSID001160221;(2Z,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal;69877-39-0

Chemical Property of (2Z,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 244.146329876
• Heavy Atom Count: 18
• Complexity: 330

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1C=CC(=CC=O)C)C)C)OC
• Isomeric SMILES: CC1=CC(=C(C(=C1/C=C/C(=C\C=O)/C)C)C)OC

Technology Process of (2Z,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal

There total 5 articles about (2Z,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal 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:

(4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylidenepent-4-enal (478496-90-1) → (2Z,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal (69877-39-0,419534-29-5) + 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al (69877-38-9,419534-29-5)

Guidance literature:

With triethylamine; In diethyl ether; at 20 ℃; for 24h;

DOI:10.1002/1522-2675(200209)85:9<2926::AID-HLCA2926>3.0.CO;2-5

Reference yield:

trimethyl phosphonoacetate (5927-18-4) + 1-(2,5,6-trimethyl-4-methoxyphenyl)-but-1-en-3-one (62924-31-6) → (2Z,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal (69877-39-0,419534-29-5) + 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al (69877-38-9,419534-29-5)

Guidance literature:

Multistep reaction;

DOI:10.1021/jm00195a010

Reference yield:

(1E)-5,5-dimethoxy-1-(4-methoxy-2,3,6-trimethylphenyl)pent-1-en-3-one (478496-91-2) → (2Z,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal (69877-39-0,419534-29-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: t-BuOK / cyclohexane / 1.5 h / Heating

1.2: 75 percent / cyclohexane / 1 h / 20 °C

2.1: 88 percent / HCO₂H / cyclopentane / 1.5 h / 20 °C

3.1: Et₃N / diethyl ether / 24 h / 20 °C

With formic acid; potassium tert-butylate; triethylamine; In diethyl ether; Cyclopentane; cyclohexane; 1.2: Wittig reaction;

DOI:10.1002/1522-2675(200209)85:9<2926::AID-HLCA2926>3.0.CO;2-5

upstream raw materials:

trimethyl phosphonoacetate

1-(2,5,6-trimethyl-4-methoxyphenyl)-but-1-en-3-one

(4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylidenepent-4-enal

(1E)-5,5-dimethoxy-1-(4-methoxy-2,3,6-trimethylphenyl)pent-1-en-3-one

Downstream raw materials:

(2Z,4E,6Z,8E)-2-Fluoro-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester