(2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal

Base Information

• Chemical Name: (2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal
• CAS No.: 121077-53-0
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.226
• Mol file: 121077-53-0.mol

Synonyms:(2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal

Chemical Property of (2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal

There total 3 articles about (2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal 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: 52.0%

5-(4-methoxyphenyl)-4-pentynal (873961-36-5) → (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienal (49678-07-1) + (2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal (121077-53-0)

Guidance literature:

With 1,6-bis(diphenylphosphino)hexane; sodium acetate; palladium diacetate; acetic acid; In 1,4-dioxane; at 90 ℃; for 16h; Overall yield = 52 %; Overall yield = 19.4 mg; diastereoselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1039/c7cc02767b

Reference yield:

4-methoxyphenylacetylen (768-60-5) → (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienal (49678-07-1) + (2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal (121077-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; trimethylphosphane / toluene; acetone / 5 h / 60 °C / Inert atmosphere

2: palladium diacetate; 1,6-bis(diphenylphosphino)hexane; sodium acetate; acetic acid / 1,4-dioxane / 16 h / 90 °C / Sealed tube; Inert atmosphere

With 1,6-bis(diphenylphosphino)hexane; sodium acetate; palladium diacetate; acetic acid; trimethylphosphane; In 1,4-dioxane; acetone; toluene;

DOI:10.1039/c7cc02767b

Reference yield:

4-methoxy-benzaldehyde (123-11-5) + (5-aza-5-cyclohexylpenta-2,4-dienyl)diethoxyphosphin-1-one (129422-73-7) → (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienal (49678-07-1) + (2E,4Z)-5-(4-Methoxy-phenyl)-penta-2,4-dienal (121077-52-9) + (2Z,4E)-5-(4-methoxyphenyl)penta-2,4-dienal (121077-53-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; Yields of byproduct given; 1.) -78 deg C, 1 h, 2.) 25 deg C, 15 h;

upstream raw materials:

4-methoxy-benzaldehyde

(5-aza-5-cyclohexylpenta-2,4-dienyl)diethoxyphosphin-1-one

5-(4-methoxyphenyl)-4-pentynal

4-methoxyphenylacetylen