methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate

Base Information

• Chemical Name: methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate
• CAS No.: 32252-91-8
• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.252
• Mol file: 32252-91-8.mol

Synonyms:methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate

Chemical Property of methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate

There total 3 articles about methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate 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: 90.0%

pyruvic acid methyl ester (600-22-6) + dimethyl [2-(4-methylphenyl)-2-oxoethyl]phosphonate (51638-13-2) → methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate (32252-91-8)

Guidance literature:

dimethyl [2-(4-methylphenyl)-2-oxoethyl]phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 0.5h; Inert atmosphere;

pyruvic acid methyl ester; In tetrahydrofuran; hexane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01618

Reference yield:

4-methyl-benzoic acid methyl ester (99-75-2) → methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate (32252-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / hexane; tetrahydrofuran / -20 - 20 °C / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/acs.orglett.0c01618

Reference yield:

→ methyl (E)-2-methyl-4-oxo-4-(p-tolyl)but-2-enoate (32252-91-8)

Guidance literature:

entspr. Saeure, CH2N2;

DOI:10.1039/j29710000156

upstream raw materials:

4-methyl-benzoic acid methyl ester

pyruvic acid methyl ester

dimethyl [2-(4-methylphenyl)-2-oxoethyl]phosphonate

Downstream raw materials:

(E)-2-methyl-4-(4-methylphenyl)-4-oxo-2-butenoic acid

Refernces