Pentanoic acid, 5-[(4-methoxyphenyl)methoxy]-, (3Z,6Z)-3,6-dodecadienyl ester

Base Information

• Chemical Name: Pentanoic acid, 5-[(4-methoxyphenyl)methoxy]-, (3Z,6Z)-3,6-dodecadienyl ester
• CAS No.: 356789-99-6
• Molecular Formula: C25H38O4
• Molecular Weight: 402.574
• Mol file: 356789-99-6.mol

Synonyms:

Chemical Property of Pentanoic acid, 5-[(4-methoxyphenyl)methoxy]-, (3Z,6Z)-3,6-dodecadienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pentanoic acid, 5-[(4-methoxyphenyl)methoxy]-, (3Z,6Z)-3,6-dodecadienyl ester

There total 10 articles about Pentanoic acid, 5-[(4-methoxyphenyl)methoxy]-, (3Z,6Z)-3,6-dodecadienyl 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: 60.0%

(Z,Z)-3,6-dodecadien-1-ol (29125-78-8) + 5-(4-methoxy-benzyloxy)-pentanoic acid (343217-75-4) → 5-(4-Methoxy-benzyloxy)-pentanoic acid (3Z,6Z)-dodeca-3,6-dienyl ester (356789-99-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0957-4166(01)00381-0

Reference yield:

1-Bromopentane (110-53-2) → 5-(4-Methoxy-benzyloxy)-pentanoic acid (3Z,6Z)-dodeca-3,6-dienyl ester (356789-99-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 70 percent / lithium amide / liquid ammonia; tetrahydrofuran; hexamethylphosphoric acid triamide / 6 h

2.1: hydrogen / Lindlar catalyst / ethanol

3.1: 85 percent / I₂; imidazole; triphenylphosphine / acetonitrile; diethyl ether / 0.75 h / 20 °C

4.1: 6 g / acetonitrile / 48 h / 60 °C

5.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / 0 °C

5.2: 60 percent / PTSA / methanol / 1 h / 20 °C

6.1: 60 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; lithium amide; hydrogen; iodine; dicyclohexyl-carbodiimide; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; ammonia; acetonitrile;

DOI:10.1016/S0957-4166(01)00381-0

Reference yield:

3-nonyn-1-ol (31333-13-8) → 5-(4-Methoxy-benzyloxy)-pentanoic acid (3Z,6Z)-dodeca-3,6-dienyl ester (356789-99-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen / Lindlar catalyst / ethanol

2.1: 85 percent / I₂; imidazole; triphenylphosphine / acetonitrile; diethyl ether / 0.75 h / 20 °C

3.1: 6 g / acetonitrile / 48 h / 60 °C

4.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / 0 °C

4.2: 60 percent / PTSA / methanol / 1 h / 20 °C

5.1: 60 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; hydrogen; iodine; dicyclohexyl-carbodiimide; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1016/S0957-4166(01)00381-0

upstream raw materials:

(Z,Z)-3,6-dodecadien-1-ol

5-(4-methoxy-benzyloxy)-pentanoic acid

1 ,5-pentanediol

3-nonyn-1-ol

Refernces

• 1、 Yadav,Nanda,Bhaskar Rao. "Soybean lipoxygenase and horseradish peroxidase catalysed asymmetric oxidation-reduction sequence for the synthesis of chiral (Z,E) diene-diols". . p. 787 - 788. Retrieved 2007/10/03.