methyl 5-(o-tolyl)-5-hexenoate

Base Information

• Chemical Name: methyl 5-(o-tolyl)-5-hexenoate
• CAS No.: 1393539-44-0
• Molecular Formula: C₁₄H₁₈O₂
• Molecular Weight: 218.296
• Mol file: 1393539-44-0.mol

Synonyms:methyl 5-(o-tolyl)-5-hexenoate

Chemical Property of methyl 5-(o-tolyl)-5-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl 5-(o-tolyl)-5-hexenoate

There total 3 articles about methyl 5-(o-tolyl)-5-hexenoate 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: 87.0%

2-Methylphenylboronic acid (16419-60-6) + methyl 5-bromohex-5-enoate → methyl 5-(o-tolyl)-5-hexenoate (1393539-44-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In water; toluene; at 80 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.151756

Reference yield: 87.0%

methyl 5-hexenoate (2396-80-7) + 2-methylphenyl triflate (66107-34-4) → methyl 5-(o-tolyl)-5-hexenoate (1393539-44-0)

Guidance literature:

With 1,1'-bis(diisopropylphosphino)ferrocene; hexamethylenetetramine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl acetamide; at 80 ℃; for 48h; Inert atmosphere;

DOI:10.1002/anie.201201806

Reference yield:

ortho-cresol (95-48-7,77504-84-8) → methyl 5-(o-tolyl)-5-hexenoate (1393539-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 5 h / 0 - 25 °C / Inert atmosphere

2: 1,1'-bis(diisopropylphosphino)ferrocene; hexamethylenetetramine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / N,N-dimethyl acetamide / 48 h / 80 °C / Inert atmosphere

With 1,1'-bis(diisopropylphosphino)ferrocene; hexamethylenetetramine; triethylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl acetamide; 2: Mizoroki-Heck reaction;

DOI:10.1002/anie.201201806

upstream raw materials:

methyl 5-hexenoate

2-methylphenyl triflate

ortho-cresol

2-Methylphenylboronic acid

Refernces

• 1、 Qin, Liena,Ren, Xinfeng,Lu, Yunpeng,Li, Yongxin,Zhou, Jianrong. "Intermolecular mizoroki-heck reaction of aliphatic olefins with high selectivity for substitution at the internal position". supporting information; experimental part. p. 5915 - 5919. Retrieved 2012/07/30.