Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Base Information

• Chemical Name: Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS No.: 13373-29-0
• Molecular Formula: C₁₃H₁₃NO₄
• Molecular Weight: 247.251
• DSSTox Substance ID: DTXSID901268276
• Mol file: 13373-29-0.mol

Synonyms:ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate;Ethyl alpha-cyano-4-hydroxy-3-methoxycinnamate;SCHEMBL2270723;DTXSID901268276;2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester

Chemical Property of Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Chemical Property:

• Vapor Pressure: 2.82E-07mmHg at 25°C
• Boiling Point: 409.1°Cat760mmHg
• Flash Point: 201.2°C
• Density: 1.242g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 247.08445790
• Heavy Atom Count: 18
• Complexity: 368

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

There total 6 articles about Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-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%

vanillin (121-33-5,8014-42-4) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester (132464-93-8,13373-29-0)

Guidance literature:

With polymer supported poly(propylene imine)dendrimer; In ethanol; at 20 ℃; for 0.166667h; Green chemistry;

DOI:10.1016/j.tetlet.2014.02.084

Reference yield: 79.0%

1-(4-vanillylidenamino-phenyl)-ethanone (85111-79-1) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester (132464-93-8,13373-29-0)

Guidance literature:

With pyridine; In benzene; for 0.25h; Heating;

Reference yield: 77.0%

4-hydroxy-3-methoxybenzaldehyde dimethylacetal (59276-35-6) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester (132464-93-8,13373-29-0)

Guidance literature:

With poly(styrenesulfonic acid-co-4-vinylpyridine) trapped into mesoporous carbon CMK-3; In water; at 60 ℃; for 1.75h;

DOI:10.1007/s11164-020-04153-4

upstream raw materials:

ethanol

2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

vanillin

ethyl 2-cyanoacetate

Downstream raw materials:

3-(4-hydroxy-3-methoxyphenyl)propionic acid

2-cyano-3-(diethoxy-phosphoryl)-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester

6-(4-hydroxy-3-methoxyphenyl)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[4,3-b]pyridine-5-carbonitrile

C₂₀H₁₇ClFN₃O₄S

Refernces

• 1、 Javad Kalbasi, Roozbeh,Rahmati, Fatemeh,Mazaheri, Omid. "Overcoming acid–base copolymer neutralization using mesoporous carbon and its catalytic activity in the tandem deacetalization–Knoevenagel condensation reaction". . p. 3413 - 3430. Retrieved 2020/05/16.
• 2、 Wen, Haimeng,Xie, Jingyan,Zhou, Yang,Zhou, Yu,Wang, Jun. "Straightforward synthesis of MTW-type magnesium silicalite for CO2 fixation with epoxides under mild conditions". . p. 5725 - 5735. Retrieved 2019/10/23.