Ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate

Base Information

• Chemical Name: Ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate
• CAS No.: 859843-60-0
• Molecular Formula: C13H13NO7
• Molecular Weight: 295.24
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID70458478
• Nikkaji Number: J2.191.787G
• Wikidata: Q82281761
• Mol file: 859843-60-0.mol

Synonyms:Ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate;859843-60-0;Ethyl 2,4-dioxo-4-(2-hydroxy-5-methyl-3-nitrophenyl)butanoate;DTXSID70458478;MFCD08443987;AKOS005072141;CA-0874;CS-0456499;J-520916;Ethyl4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate;4-(2-Hydroxy-3-nitro-5-methylphenyl)-2,4-dioxobutanoic acid ethyl ester

Chemical Property of Ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate

Chemical Property:

• Melting Point: 116-118°C
• PSA: 126.49000
• LogP: 1.83700
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 295.06920175
• Heavy Atom Count: 21
• Complexity: 442

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 2,4-dioxo-4-(2-hydroxy-5-methyl-3-nitrophenyl)butanoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=O)CC(=O)C1=C(C(=CC(=C1)C)[N+](=O)[O-])O

Technology Process of Ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate

There total 2 articles about Ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate 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: 86.0%

2-hydroxy-5-methyl-3-nitroacetophenone (66108-30-3) + oxalic acid diethyl ester (95-92-1) → ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate (859843-60-0)

Guidance literature:

2-hydroxy-5-methyl-3-nitroacetophenone; With sodium ethanolate; In ethanol; for 0.5h;

oxalic acid diethyl ester; In ethanol; for 2h; Heating;

DOI:10.1081/SCC-200057984

Reference yield:

5-methyl-2-hydroxyacetophenone (1450-72-2) → ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate (859843-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 63 percent / glacial acetic acid; nitric acid / 15 - 20 °C

2.1: sodium ethoxide / ethanol / 0.5 h

2.2: 86 percent / ethanol / 2 h / Heating

With nitric acid; sodium ethanolate; acetic acid; In ethanol; 2.2: Claisen condensation;

DOI:10.1081/SCC-200057984

Reference yield:

ethyl 4-(2-hydroxy-5-methyl-3-nitrophenyl)-2,4-dioxobutanoate (859843-60-0) → ethyl 8-[(4-cyanobenzoyl)amino]-6-methyl-2-chromanecarboxylate (859843-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / glacial acetic acid; HCl / 2 h / 80 °C

2: 80 percent / HCl; hydrogen / palladium on activated charcoal / ethanol / 53 h / 50 - 60 °C / 5250.42 - 7500.6 Torr

3: 68 percent / triethylamine / CH₂Cl₂ / 6 h / -10 - 20 °C

With hydrogenchloride; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1081/SCC-200057984

upstream raw materials:

2-hydroxy-5-methyl-3-nitroacetophenone

oxalic acid diethyl ester

5-methyl-2-hydroxyacetophenone

Downstream raw materials:

ethyl 8-[(4-cyanobenzoyl)amino]-6-methyl-2-chromanecarboxylate

ethyl 6-methyl-8-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2-chromanecarboxylate