2-Acetyl-3-(4-hydroxy-phenyl)-acrylic acid ethyl ester

Base Information

• Chemical Name: 2-Acetyl-3-(4-hydroxy-phenyl)-acrylic acid ethyl ester
• CAS No.: 58714-57-1
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• DSSTox Substance ID: DTXSID701223121
• Mol file: 58714-57-1.mol

Synonyms:CBMicro_007095;SCHEMBL7700123;DTXSID701223121;AKOS030660123;ethyl 2-(4-hydroxybenzylidene)-3-oxobutanoate;Ethyl 2-[(4-hydroxyphenyl)methylene]-3-oxobutanoate;2-acetyl-3-(4-hydroxy-phenyl)-acrylic acid ethyl ester;58714-57-1

Chemical Property of 2-Acetyl-3-(4-hydroxy-phenyl)-acrylic acid ethyl ester

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 234.08920892
• Heavy Atom Count: 17
• Complexity: 311

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(=CC1=CC=C(C=C1)O)C(=O)C

Technology Process of 2-Acetyl-3-(4-hydroxy-phenyl)-acrylic acid ethyl ester

There total 8 articles about 2-Acetyl-3-(4-hydroxy-phenyl)-acrylic acid ethyl 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: 95.0%

ethyl acetoacetate (141-97-9) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → E-2-(4-Hydroxybenzyliden)acetessigsaeure-ethylester (58714-57-1)

Guidance literature:

With piperidine; acetic acid;

DOI:10.1016/j.tetlet.2012.05.149

Reference yield: 35.0%

ethyl 2-(4-methoxybenzylidene)-3-oxobutanoate (24405-45-6,24405-46-7,15725-26-5) → E-2-(4-Hydroxybenzyliden)acetessigsaeure-ethylester (58714-57-1)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 18h;

DOI:10.1007/s12039-013-0489-4

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → E-2-(4-Hydroxybenzyliden)acetessigsaeure-ethylester (58714-57-1)

Guidance literature:

Multi-step reaction with 2 steps

1: piperdinium acetate / toluene / 16 h / Dean-Stark; Reflux

2: boron tribromide / dichloromethane / 18 h / 0 - 20 °C

With boron tribromide; piperdinium acetate; In dichloromethane; toluene; 1: |Knoevenagel Condensation;

DOI:10.1007/s12039-013-0489-4

upstream raw materials:

ethyl acetoacetate

4-hydroxy-benzaldehyde

4-methoxy-benzaldehyde

ethyl 2-(4-methoxybenzylidene)-3-oxobutanoate

Downstream raw materials:

2-(4-Hydroxybenzyl)acetessigsaeure-ethylester

2-[4-[(1,2-dihydro-2-oxoquinolin-4-yl)methoxy]phenylmethylene]-3-oxobutanoic acid ethyl ester

2-[4-[(1,2-dihydro-8-methyl-2-oxoquinolin-4-yl)methoxy]phenylmethylene]-3-oxobutanoic acid ethyl ester

2-[4-[(7-chloro-1,2-dihydro-2-oxoquinolin-4-yl)methoxy]phenylmethylene]-3-oxobutanoic acid ethyl ester