(1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene

Base Information

• Chemical Name: (1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene
• CAS No.: 53598-04-2
• Molecular Formula: C₁₇H₂₂
• Molecular Weight: 226.362
• Mol file: 53598-04-2.mol

Synonyms:(1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene

Chemical Property of (1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene

There total 10 articles about (1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene 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: 77.0%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) + benzaldehyde (100-52-7) → (1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene (53598-04-2)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1021/ja906083c

Reference yield: 40.0%

Geraniol (106-24-1) + benzaldehyde (100-52-7) → 4,8-Dimethyl-1-phenylnona-1,3,7-trien (53163-68-1,53598-04-2,60976-12-7)

Guidance literature:

With tributylphosphine; phenyl isocyanate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; for 5h; Heating;

DOI:10.1246/cl.1988.1449

Reference yield:

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1) → (1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene (53598-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBr / Pd(PPh₃)4 / tetrahydrofuran; methanol / 2 h / Heating

2: 1) BuLi / 1) THF-hexane, room temperature, 30 min, 2) room temperature, overnight

With n-butyllithium; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol;

DOI:10.1246/bcsj.57.3013

upstream raw materials:

Geraniol

benzaldehyde

trans-geranyl bromide

benzyl phenyl sulfoxide

Refernces

• 1、 Okukado, Nobuhisa,Uchikawa, Osamu,Nakamura, Yukari. "Palladium-Catalyzed Allylidenation of Aldehyde. A Simple and Convenient Method for the Preparation of Conjugated Diene and Polyene Compounds". . p. 1449 - 1452. Retrieved 2007/10/02.
• 2、 Inoue, Yoshio,Toyofuku, Masanori,Hashimoto, Harukichi. "2-Allylisourea as a Starting Material for Palladium-Catalyzed Wittig-Type Allylidenation of Aldehydes". . p. 1279 - 1280. Retrieved 2007/10/02.