(Z)-ethyl 3-(3-methylphenyl)-but-2-enoate

Base Information

• Chemical Name: (Z)-ethyl 3-(3-methylphenyl)-but-2-enoate
• CAS No.: 1193381-11-1
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.269
• Mol file: 1193381-11-1.mol

Synonyms:(Z)-ethyl 3-(3-methylphenyl)-but-2-enoate

Chemical Property of (Z)-ethyl 3-(3-methylphenyl)-but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (Z)-ethyl 3-(3-methylphenyl)-but-2-enoate

There total 3 articles about (Z)-ethyl 3-(3-methylphenyl)-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: 100.0%

(E)-ethyl 3-(3-methylphenyl)-but-2-enoate (433732-56-0) → (Z)-ethyl 3-(3-methylphenyl)-but-2-enoate (1193381-11-1)

Guidance literature:

With copper diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In ethyl acetate; at 20 ℃; for 24h; Glovebox; Inert atmosphere; Irradiation; Sealed tube;

DOI:10.1021/acs.orglett.0c02894

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-Methylacetophenone (585-74-0) → (Z)-ethyl 3-(3-methylphenyl)-but-2-enoate (1193381-11-1) + (E)-ethyl 3-(3-methylphenyl)-but-2-enoate (433732-56-0)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;

3-Methylacetophenone; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 24h; Overall yield = 75 %; Overall yield = 3.06 g; Inert atmosphere;

DOI:10.1039/c8ob00731d

Reference yield:

3-Methylacetophenone (585-74-0) → (Z)-ethyl 3-(3-methylphenyl)-but-2-enoate (1193381-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: copper diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / ethyl acetate / 24 h / 20 °C / Glovebox; Inert atmosphere; Irradiation; Sealed tube

With copper diacetate; sodium hydride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; ethyl acetate; mineral oil;

DOI:10.1021/acs.orglett.0c02894

upstream raw materials:

(E)-ethyl 3-(3-methylphenyl)-but-2-enoate

diethoxyphosphoryl-acetic acid ethyl ester

3-Methylacetophenone