4-Hydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 4-Hydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester
• CAS No.: 1821-20-1
• Molecular Formula: C12H10O5
• Molecular Weight: 234.208
• Hs Code.: 2932209090
• Mol file: 1821-20-1.mol

Synonyms:3-carbethoxy-4-hydroxy-coumarin;ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate;3-ethoxycarbonyl-4-hydroxycoumarin;4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester;

Chemical Property of 4-Hydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester

Chemical Property:

• Vapor Pressure: 3.71E-06mmHg at 25°C
• Melting Point: 139-140 °C
• Boiling Point: 370.9°C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 144.2°C
• PSA: 76.74000
• Density: 1.41g/cm³
• LogP: 1.67530
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

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

ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Hydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester

There total 7 articles about 4-Hydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester 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: 79.0%

1,3-diethyl 2-diazopropanedioate (5256-74-6) + salicylaldehyde (90-02-8) → ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate (1821-20-1)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid; In 1,2-dichloro-ethane; at 70 ℃; for 24h; Temperature; Reagent/catalyst; Solvent; Catalytic behavior;

DOI:10.1039/c8nj04576c

Reference yield: 66.0%

ethyl [(2-acetoxyphenyl)hydroxymethylidene]ethoxycarbonylacetate (770719-70-5) → ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate (1821-20-1)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 48h;

DOI:10.1055/s-2004-829132

Reference yield:

acetylsalicylic acid N-hydroxysuccinimide ester (84388-73-8) → ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate (1821-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: ethanol; sodium / 24 h / 20 °C

With ethanol; sodium; sodium hydride; In tetrahydrofuran; mineral oil;

DOI:10.3390/molecules16010384

upstream raw materials:

diethyl malonate

O-acetylsalicyloyl chloride

ethyl [(2-acetoxyphenyl)hydroxymethylidene]ethoxycarbonylacetate

diethyl 2-(2-acetoxy)benzoylmalonate

Downstream raw materials:

ethyl 4-(benzyl(2-(cyclohexylamino)-2-oxo-1-phenylethyl)amino)-2-oxo-2H-chromene-3-carboxylate

4-chloro-2-oxo-2H-chromene-3-carboxylic acid ethyl ester

4-hydroxy[1]benzopyran-2-one

4-hydroxy-3-(1-(4-methoxyphenyl)-3-oxobutyl)-2H-chromen-2-one

Refernces

• 1、 Stefanou, Valentina,Matiadis, Dimitris,Melagraki, Georgia,Afantitis, Antreas,Athanasellis, Giorgos,Igglessi-Markopoulou, Olga,McKee, Vickie,Markopoulos, John. "Functionalized 4-hydroxy coumarins: Novel synthesis, crystal structure and DFT calculations". experimental part. p. 384 - 402. Retrieved 2011/03/22.
• 2、 Athanasellis, Giorgos,Melagraki, Georgia,Chatzidakis, Haralambos,Afantitis, Antreas,Detsi, Anastasia,Igglessi-Markopoulou, Olga,Markopoulos, John. "Novel short-step synthesis of functionalized γ-phenyl-β- hydroxybutenoates and their cyclization to 4-hydroxycoumarins via the N-hydroxybenzotriazole methodology". . p. 1775 - 1782. Retrieved 2007/10/03.