2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone

Base Information

• Chemical Name: 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone
• CAS No.: 109471-14-9
• Molecular Formula: C₁₈H₁₈O₅
• Molecular Weight: 314.338
• Mol file: 109471-14-9.mol

Synonyms:2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone

Chemical Property of 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone

There total 5 articles about 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone 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: 75.9%

2-hydroxy-4-(methoxymethoxy)acetophenone (65490-08-6) + 4-methoxy-benzaldehyde (123-11-5) → 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone (109471-14-9)

Guidance literature:

With potassium hydroxide; In ethanol; at 0 - 20 ℃;

DOI:10.1016/j.ejmech.2017.02.037

Reference yield: 68.0%

2-hydroxy-4-(methoxymethoxy)acetophenone (65490-08-6) + 4-methoxy-benzaldehyde (123-11-5) → (2E)-1-[2-hydroxy-4-(methoxymethoxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one (109471-14-9)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/acs.joc.1c01375

Reference yield:

2',4'-dihydroxy-4-acetophenone (89-84-9) → 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone (109471-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / acetone / 2 h / 30 °C

2: potassium hydroxide / ethanol; water / 36 h / 20 °C

With potassium carbonate; potassium hydroxide; In ethanol; water; acetone; 2: Claisen-Schmidt condensation;

DOI:10.1016/j.bmc.2011.03.063

upstream raw materials:

2-hydroxy-4-(methoxymethoxy)acetophenone

4-methoxy-benzaldehyde

2',4'-dihydroxy-4-acetophenone

recorcinol

Downstream raw materials:

(Z)-2-(4-methoxybenzylidene)-6-(methoxymethoxy)benzo[b]furan-3-one

(Z)-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-6-yl (10E,12Z)-linoleate

(Z)-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-6-yl stearate

(Z)-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-6-yl 10-undecylenate

Refernces

• 1、 Kwesiga, George,Schmidt, Bernd,Sperlich, Eric. "Scope and Applications of 2,3-Oxidative Aryl Rearrangements for the Synthesis of Isoflavone Natural Products". . p. 10699 - 10712. Retrieved 2021/08/20.
• 2、 Zhang, Guoning,Liu, Shuainan,Tan, Wenjuan,Verma, Ruchi,Chen, Yuan,Sun, Deyang,Huan, Yi,Jiang, Qian,Wang, Xing,Wang, Na,Xu, Yang,Wong, Chiwai,Shen, Zhufang,Deng, Ruitang,Liu, Jinsong,Zhang, Yanqiao,Fang, Weishuo. "Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists". . p. 303 - 309. Retrieved 2017/03/01.