(E)-p-methylcinnamyl chloride

Base Information

• Chemical Name: (E)-p-methylcinnamyl chloride
• CAS No.: 96000-21-4
• Molecular Formula: C₁₀H₁₁Cl
• Molecular Weight: 166.65
• Mol file: 96000-21-4.mol

Synonyms:(E)-p-methylcinnamyl chloride

Chemical Property of (E)-p-methylcinnamyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-p-methylcinnamyl chloride

There total 15 articles about (E)-p-methylcinnamyl chloride 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: 95.0%

1-(4-methylphenyl)-2-propen-1-ol (58824-48-9) → (E)-p-methylcinnamyl chloride (96000-21-4)

Guidance literature:

With thionyl chloride; In dichloromethane; at 20 ℃; Inert atmosphere; Cooling;

DOI:10.1021/ja2075967

Reference yield: 88.0%

p-methylcinnamyl alcohol (122058-30-4) → (E)-p-methylcinnamyl chloride (96000-21-4)

Guidance literature:

With thionyl chloride; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201912618

Reference yield:

ethyl (E)-3-(4-methylphenyl)acrylate (97585-04-1,20511-20-0,24393-49-5) → (E)-p-methylcinnamyl chloride (96000-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄; diethyl ether / -18 °C

2: SOCl₂; pyridine; CHCl₃

With pyridine; lithium aluminium tetrahydride; thionyl chloride; diethyl ether; chloroform;

upstream raw materials:

4-methylcinnamyl alcohol

3-(4-methylphenyl)acrylaldehyde

4-methylphenylallene

4-methyl-benzaldehyde

Downstream raw materials:

4-methyl-cinnamaldehyde

3-(4-methylphenyl)prop-2-enyl acetate

6-(p-Methylphenyl)-3-phenyl-5-hexen-2-on

4-methylcinnamyl alcohol

Refernces

• 1、 Jette, Carina I.,Tong, Z. Jaron,Hadt, Ryan G.,Stoltz, Brian M.. "Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal". supporting information. p. 2033 - 2038. Retrieved 2020/01/02.
• 2、 Tian, Qinqin,Liu, Yulong,Wang, Xiaoyun,Wang, Xie,He, Wei. "PdII/Novel Chiral Cinchona Alkaloid Oxazoline-Catalyzed Enantioselective Oxidative Cyclization of Aromatic Alkenyl Amides". supporting information. p. 3850 - 3855. Retrieved 2019/06/08.