2-Hydroxy-beta-oxobenzenepropanal

Base Information

• Chemical Name: 2-Hydroxy-beta-oxobenzenepropanal
• CAS No.: 14386-66-4
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• DSSTox Substance ID: DTXSID101306024
• Nikkaji Number: J679.408D
• Mol file: 14386-66-4.mol

Synonyms:2-Hydroxy-beta-oxobenzenepropanal;14386-66-4;SCHEMBL2556609;DTXSID101306024;AKOS006332230;3-(2-hydroxyphenyl)-3-oxo-propionaldehyde

Chemical Property of 2-Hydroxy-beta-oxobenzenepropanal

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 2-Hydroxy-beta-oxobenzenepropanal

There total 8 articles about 2-Hydroxy-beta-oxobenzenepropanal 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: 60.0%

o-hydroxyacetophenone (118-93-4,104809-67-8) + formic acid ethyl ester (109-94-4) → 2-(formylacetyl)phenol (14386-66-4)

Guidance literature:

With sodium; In hexane; Reflux;

DOI:10.1016/j.bioorg.2013.07.001

Reference yield: 2.0%

2,3-dihydro-2-hydroxy-4H-1-benzopyran-4-one (57669-32-6) → 2-(formylacetyl)phenol (14386-66-4) + ω-formyl-2'-hydroxyacetophenone (87059-79-8)

Guidance literature:

In chloroform-d1; for 200h; Product distribution; Ambient temperature; equilibrium. Var_. time;

DOI:10.1016/S0040-4039(01)81693-2

Reference yield:

1-benzopyran-4(4H)-one (491-38-3) → formic acid (64-18-6) + 2-(formylacetyl)phenol (14386-66-4) + 2,3-dihydro-2-hydroxy-4H-1-benzopyran-4-one (57669-32-6) + o-hydroxyacetophenone (118-93-4,104809-67-8) + acetaldehyde (75-07-0,9002-91-9) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

With 1.) alkali 2.) acid; for 48h; Product distribution; Mechanism; Ambient temperature; further derivatives, further products;

upstream raw materials:

1-benzopyran-4(4H)-one

2,3-dihydro-2-hydroxy-4H-1-benzopyran-4-one

o-hydroxyacetophenone

formic acid ethyl ester

Downstream raw materials:

1-benzopyran-4(4H)-one

trans-1-(2-Hydroxybenzoyl)-2-(4-oxo-4H-<1>benzopyran-3-yl)-ethylen

3-(2-hydroxyphenyl)-1-methyl-1H-pyrazole

1-acetoxy-2-isoxazol-3-yl-benzene

Refernces

• 1、 Eiden,Haverland. "Concerning the reafion of O-hydroxy-omega-formyl-acetophenone with aldehydes". . p. 2554 - 2560. Retrieved 1967.
• 2、 Talhi, Oualid,Brodziak-Jarosz, Lidia,Panning, Jana,Orlikova, Barbora,Zwergel, Clemens,Tzanova, Tzvetomira,Philippot, Stéphanie,Pinto, Diana C. G. A.,Paz, Filipe A. Almeida,Gerhaüser, Clarissa,Dick, Tobias P.,Jacob, Claus,Diederich, Marc,Bagrel, Denyse,Kirsch, Gilbert,Silva, Artur M. S.. "One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential". . p. 965 - 975. Retrieved 2016/03/01.
• 3、 Liu, Jie,Li, Zhanchao,Tong, Pei,Xie, Zhixiang,Zhang, Yuan,Li, Ying. "TMSI-Promoted vinylogous michael addition of siloxyfuran to 2-substituted chromones: A general approach for the total synthesis of chromanone lactone natural products". supporting information. p. 1632 - 1643. Retrieved 2015/02/19.