5-(p-tolyl)pent-4-enoic acid

Base Information

• Chemical Name: 5-(p-tolyl)pent-4-enoic acid
• CAS No.: 5724-05-0
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.242
• Mol file: 5724-05-0.mol

Synonyms:5-(p-tolyl)pent-4-enoic acid

Chemical Property of 5-(p-tolyl)pent-4-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(p-tolyl)pent-4-enoic acid

There total 12 articles about 5-(p-tolyl)pent-4-enoic acid 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:

ethyl (E)-3-(4-methylphenyl)acrylate (97585-04-1,20511-20-0,24393-49-5) → (E)-5-(4-methylphenyl)pent-4-enoic acid (5724-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere

2.1: phosphorus tribromide / diethyl ether / 0 °C / Inert atmosphere; Darkness

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

3.2: 20 h / 0 - 20 °C

4.1: potassium hydroxide / methanol; water / 21 h / 110 °C

4.2: 170 - 190 °C

With phosphorus tribromide; sodium hydride; diisobutylaluminium hydride; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; mineral oil;

DOI:10.1002/anie.201808320

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + 1-(cyclopropylidenemethyl)-4-methylbenzene (55088-80-7) → p-Methyl-α-ethyl-zimtsaeure (27687-43-0) + (E)-5-(4-methylphenyl)pent-4-enoic acid (5724-05-0)

Guidance literature:

With 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 0 ℃; for 4h; under 3800.26 Torr; Title compound not separated from byproducts.;

DOI:10.1039/b515684j

Reference yield:

4-methyl-benzaldehyde (104-87-0) + (3-carboxypropyl)(triphenyl)phosphonium bromide (17857-14-6) → (E)-5-(4-methylphenyl)pent-4-enoic acid (5724-05-0)

Guidance literature:

(3-carboxypropyl)(triphenyl)phosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -20 ℃; for 0.333333h;

4-methyl-benzaldehyde; In tetrahydrofuran; at -78 ℃; for 18h;

DOI:10.1021/ol200840e

upstream raw materials:

carbon dioxide

1-(cyclopropylidenemethyl)-4-methylbenzene

4-methyl-benzaldehyde

(3-carboxypropyl)(triphenyl)phosphonium bromide

Downstream raw materials:

(5R,6S)-5-bromo-6-p-tolyltetrahydro-2H-pyran-2-one

(E)-5-p-tolylpent-4-enyl methanesulfonate

(+/-)-5-(4-methylphenylcarbonyl)dihydrofuran-2(3H)-one

5-(p-tolyl)pentanoyl chloride

Refernces

• 1、 Einaru, Shunsuke,Shitamichi, Kenta,Nagano, Tagui,Matsumoto, Akira,Asano, Keisuke,Matsubara, Seijiro. "trans-Cyclooctenes as Halolactonization Catalysts". . p. 13863 - 13867. Retrieved 2018/09/27.
• 2、 Zhang, Qing-Bao,Ban, Yong-Liang,Zhou, Da-Gang,Zhou, Pan-Pan,Wu, Li-Zhu,Liu, Qiang. "Preparation of α-Acyloxy Ketones via Visible-Light-Driven Aerobic Oxo-Acyloxylation of Olefins with Carboxylic Acids". supporting information. p. 5256 - 5259. Retrieved 2016/11/02.