Eupatarone

Base Information

• Chemical Name: Eupatarone
• CAS No.: 17249-61-5
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.225
• Mol file: 17249-61-5.mol

Synonyms:2-acetyl-5,6-dimethoxybenzofuran;5,6-dimethoxy-2-acetylbenzofuran;caleprunin B;

Chemical Property of Eupatarone

Chemical Property:

• Vapor Pressure: 0.000224mmHg at 25°C
• Melting Point: 115-116℃ (hexane ethyl acetate )
• Boiling Point: 325.9°Cat760mmHg
• Flash Point: 150.9°C
• PSA: 48.67000
• Density: 1.184g/cm³
• LogP: 2.65260

Purity/Quality:

98%Min ^*data from raw suppliers

Eupatarone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Eupatarone

There total 14 articles about Eupatarone 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: 82.0%

2-hydroxy-4,5-dimethoxybenzaldehyde (14382-91-3) + chloroacetone (78-95-5) → (5,6-dimethoxybenzofuran-2-yl)ethan-2-one (17249-61-5)

Guidance literature:

With potassium carbonate; In acetone; for 6h; Reflux;

DOI:10.1021/ol3020013

Reference yield: 70.0%

2-hydroxy-4,5-dimethoxybenzaldehyde (14382-91-3) + 1-bromoacetone (598-31-2) → (5,6-dimethoxybenzofuran-2-yl)ethan-2-one (17249-61-5)

Guidance literature:

2-hydroxy-4,5-dimethoxybenzaldehyde; With potassium carbonate; In butanone; at 0 ℃; for 0.166667h; Inert atmosphere;

1-bromoacetone; In butanone; at 90 ℃; for 4h; Inert atmosphere;

Reference yield: 63.0%

(Z)-3-(3,4-dimethoxyphenoxy)-4-dimethylamino-3-buten-2-one (868856-45-5) → (5,6-dimethoxybenzofuran-2-yl)ethan-2-one (17249-61-5)

Guidance literature:

With iodine; In dichloromethane; at 120 ℃; for 12h; Reagent/catalyst; Inert atmosphere; Sealed tube;

DOI:10.1002/jhet.1686

upstream raw materials:

(Z)-3-(3,4-dimethoxyphenoxy)-4-dimethylamino-3-buten-2-one

1-(3,4-dimethoxyphenoxy)propan-2-one

N,N-dimethyl-formamide dimethyl acetal

3,4-dimethoxyphenol

Refernces

• 1、 Henry, Martyn C.,Sutherland, Andrew. "Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis". . p. 2766 - 2770. Retrieved 2020/03/30.
• 2、 Labarrios, Ehecatl,Jerezano, Alberto,Jimenez, Fabiola,Del Carmen Cruz, Maria,Delgado, Francisco,Zepeda, L. Gerardo,Tamariz, Joaquin. "Efficient synthetic approach to substituted benzo[b]furans and benzo[b]thiophenes by iodine-promoted cyclization of enaminones". . p. 954 - 971. Retrieved 2014/08/05.