Diethyl [(4-hydroxy-3-methoxyphenyl)methylidene]propanedioate

Base Information

• Chemical Name: Diethyl [(4-hydroxy-3-methoxyphenyl)methylidene]propanedioate
• CAS No.: 24331-83-7
• Molecular Formula: C15H18 O6
• Molecular Weight: 294.304
• NSC Number: 163812
• DSSTox Substance ID: DTXSID20303969
• Nikkaji Number: J1.607.336I
• Mol file: 24331-83-7.mol

Synonyms:24331-83-7;NSC163812;SCHEMBL934307;DTXSID20303969;Diethyl [(4-hydroxy-3-methoxyphenyl)methylidene]propanedioate;NSC-163812

Chemical Property of Diethyl [(4-hydroxy-3-methoxyphenyl)methylidene]propanedioate

Chemical Property:

• Vapor Pressure: 1.47E-06mmHg at 25°C
• Boiling Point: 387.5°Cat760mmHg
• Flash Point: 136.1°C
• Density: 1.215g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 294.11033829
• Heavy Atom Count: 21
• Complexity: 370

Purity/Quality:

99% HPLC, ^*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(=O)OCC

Technology Process of Diethyl [(4-hydroxy-3-methoxyphenyl)methylidene]propanedioate

There total 4 articles about Diethyl [(4-hydroxy-3-methoxyphenyl)methylidene]propanedioate 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: 95.2%

2-ethoxy-2-oxoethyl propionate (29751-63-1) + vanillin (121-33-5,8014-42-4) → diethyl 2-(4-hydroxy-3-methoxybenzylidene)malonate (24331-83-7)

Guidance literature:

With piperidine; benzoic acid; In toluene; for 4h; Heating;

DOI:10.1248/cpb.31.560

Reference yield: 90.0%

vanillin (121-33-5,8014-42-4) + diethyl malonate (105-53-3) → diethyl 2-(4-hydroxy-3-methoxybenzylidene)malonate (24331-83-7)

Guidance literature:

With piperidine; acetic acid; In dichloromethane; for 14h; Reflux; Dean-Stark;

DOI:10.1039/c2gc35848d

Reference yield:

3-methoxy-2-hydroxybenzaldehyde (148-53-8) + diethyl malonate (105-53-3) → diethyl 2-(4-hydroxy-3-methoxybenzylidene)malonate (24331-83-7)

Guidance literature:

With 1-n-butyl-3-methylimidazolim bromide; at 60 ℃; for 8h;

DOI:10.1002/adsc.201000870

upstream raw materials:

vanillin

diethyl malonate

2-ethoxy-2-oxoethyl propionate

3-methoxy-2-hydroxybenzaldehyde

Downstream raw materials:

(4-hydroxy-3-methoxy-benzylidene)-malonic acid

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

dihydrocaffeic acid

5-(3-Chloro-4-hydroxy-5-methoxy-benzyl)-thiazolidine-2,4-dione

Refernces

• 1、 Shrivastava, Sushant K.,Srivastava, Pavan,Bandresh, Robin,Tripathi, Prabhash Nath,Tripathi, Avanish. "Design, synthesis, and biological evaluation of some novel indolizine derivatives as dual cyclooxygenase and lipoxygenase inhibitor for anti-inflammatory activity". . p. 4424 - 4432. Retrieved 2017/07/22.
• 2、 Sharma, Nandini,Sharma, Upendra K.,Kumar, Rajesh,Katoch, Nidhi,Kumar, Rakesh,Sinha, Arun K.. "First bovine serum albumin-promoted synthesis of enones, cinnamic acids and coumarins in ionic liquid: An insight into the role of protein impurities in porcine pancreas lipase for olefinic bond formation". scheme or table. p. 871 - 878. Retrieved 2011/06/19.