(Z)-2-benzylidene-3-acetoxypropionate methyl ester

Base Information

• Chemical Name: (Z)-2-benzylidene-3-acetoxypropionate methyl ester
• CAS No.: 159763-37-8
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• Mol file: 159763-37-8.mol

Synonyms:(Z)-2-benzylidene-3-acetoxypropionate methyl ester

Chemical Property of (Z)-2-benzylidene-3-acetoxypropionate methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-benzylidene-3-acetoxypropionate methyl ester

There total 4 articles about (Z)-2-benzylidene-3-acetoxypropionate methyl ester 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:

methyl 3-hydroxy-2-methylidene-3-phenylpropionate (18020-59-2) → (Z)-2-benzylidene-3-acetoxypropionate methyl ester (159763-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / conc. sulfuric acid / 0.5 h

2: 1,4-diazabicyclo-<2,2,2>-octane / tetrahydrofuran / 0.5 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; sulfuric acid; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89311-X

Reference yield:

Methyl 3-acetoxy-2-methylene-3-phenylpropanoate (124957-36-4) → Methyl (2E)-2-(acetoxymethyl)-3-phenylprop-2-enoate (124957-42-2) + (Z)-2-benzylidene-3-acetoxypropionate methyl ester (159763-37-8)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; for 0.5h; Yield given. Yields of byproduct given; Heating;

DOI:10.1016/S0040-4020(01)89311-X

Reference yield:

methyl 2-(1-acetoxymethyl)acrylate (30982-08-2) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → Methyl (2E)-2-(acetoxymethyl)-3-phenylprop-2-enoate (124957-42-2) + (Z)-2-benzylidene-3-acetoxypropionate methyl ester (159763-37-8)

Guidance literature:

With palladium(II) trifluoroacetate; silver(I) acetate; Trimethylacetic acid; for 12h; Overall yield = 87 %; Reflux;

DOI:10.1016/j.tetlet.2012.11.026

upstream raw materials:

Methyl 3-acetoxy-2-methylene-3-phenylpropanoate

methyl 3-hydroxy-2-methylidene-3-phenylpropionate

acetic anhydride

methyl 2-(1-acetoxymethyl)acrylate

Downstream raw materials:

(E)-2-(Hydroxymethyl)-3-phenyl-2-propenoic acid