(2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester

Base Information

• Chemical Name: (2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester
• CAS No.: 177555-32-7
• Molecular Formula: C₂₁H₂₆O₂
• Molecular Weight: 310.436
• Mol file: 177555-32-7.mol

Synonyms:(2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester

Chemical Property of (2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester

There total 3 articles about (2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl 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: 74.0%

ethyl (2E)-4-(diethoxyphosphoryl)crotonate (42516-28-9) + (6E,8E)-9-Phenyl-nona-6,8-dienal (177555-31-6) → (2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester (177555-32-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -78 deg C, 20 min; 2.) -78 deg C, 10 min; to RT, 1.5 h;

DOI:10.1139/v96-046

Reference yield:

(6E,8E)-9-Phenyl-nona-6,8-dien-1-ol (177555-30-5) → (2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester (177555-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Swern oxidation

2: 74 percent / 1.) n-butyllithium / hexane; tetrahydrofuran / 1.) -78 deg C, 20 min; 2.) -78 deg C, 10 min; to RT, 1.5 h

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1139/v96-046

Reference yield:

(6E,8E)-9-Phenyl-nona-6,8-dienoic acid 3-hydroxy-propyl ester (177555-18-9) → (2E,4E,10E,12E)-13-Phenyl-trideca-2,4,10,12-tetraenoic acid ethyl ester (177555-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / 1.) LAH; 2.) NaOH, water / tetrahydrofuran / 1.) 0 deg C to RT, 3.5 h; 2.) RT, 20 min

2: 96 percent / Swern oxidation

3: 74 percent / 1.) n-butyllithium / hexane; tetrahydrofuran / 1.) -78 deg C, 20 min; 2.) -78 deg C, 10 min; to RT, 1.5 h

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; water; In tetrahydrofuran; hexane;

DOI:10.1139/v96-046

upstream raw materials:

ethyl (2E)-4-(diethoxyphosphoryl)crotonate

(6E,8E)-9-Phenyl-nona-6,8-dienal

(6E,8E)-9-Phenyl-nona-6,8-dien-1-ol

(6E,8E)-9-Phenyl-nona-6,8-dienoic acid 3-hydroxy-propyl ester

Downstream raw materials:

(2E,4E)-deca-2,4-dienoic acid

13-phenyltrideca-2E,4E,10E,12E-tetraenoic acid

(2E,4E)-N-isobutyldecadienamide

Refernces