Ethyl 3,5-dioxocyclohexanecarboxylate

Base Information

• Chemical Name: Ethyl 3,5-dioxocyclohexanecarboxylate
• CAS No.: 27513-35-5
• Molecular Formula: C9H12O4
• Molecular Weight: 184.192
• European Community (EC) Number: 865-311-3
• Mol file: 27513-35-5.mol

Synonyms:27513-35-5;ethyl 3,5-dioxocyclohexanecarboxylate;Ethyl 3,5-dioxocyclohexane-1-carboxylate;3,5-Dioxocyclohexanecarboxylic Acid Ethyl Ester;Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester;SCHEMBL6903800;RPRRICYOWFRORO-UHFFFAOYSA-N;ethyl3,5-dioxocyclohexanecarboxylate;AT29925;SB12303;ethyl 3, 5-dioxocyclohexane-1-carboxylate;CS-0183660;EN300-80461;cyclohexanecarboxylic acid,3,5-dioxo-,ethyl ester

Chemical Property of Ethyl 3,5-dioxocyclohexanecarboxylate

Chemical Property:

• Boiling Point: 125-126 °C(Press: 0.4 Torr)
• PKA: 4.42±0.20(Predicted)
• PSA: 60.44000
• Density: 1.199±0.06 g/cm3(Predicted)
• LogP: 0.48780
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Soluble), Dichloromethane (Slightly), Dimethylformamide (Slightly),
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

97% ^*data from raw suppliers

3,5-DioxocyclohexanecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC(=O)CC(=O)C1
• Uses: A reactant in the preparation of plant growth retardants and cyclopropanecarbonyloxy cyclohexenone derivs. as hydroxyphenylpyruvate dioxygenase inhibitors.

Technology Process of Ethyl 3,5-dioxocyclohexanecarboxylate

There total 6 articles about Ethyl 3,5-dioxocyclohexanecarboxylate 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:

diethyl 2-acetylmethyl-1,4-butanedioate (1187-74-2) → 5-ethoxycarbonyl-cyclohexane-1,3-dione (27513-35-5)

Guidance literature:

With base;

DOI:10.1016/S0968-0896(01)00322-4

Reference yield:

diethyl 2-ethoxysuccinate (17596-10-0) → 5-ethoxycarbonyl-cyclohexane-1,3-dione (27513-35-5)

Guidance literature:

With sodium ethanolate; In acetone; at 40 - 70 ℃; for 1h;

Reference yield:

but-2-enedioic acid diethyl ester (1520-50-9) → 5-ethoxycarbonyl-cyclohexane-1,3-dione (27513-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / 5 h

2: trifluoroacetic acid / toluene / 2 h

3: sodium ethanolate / 2 h

With sodium ethanolate; trifluoroacetic acid; potassium hydroxide; In toluene;

upstream raw materials:

diethyl 2-acetylmethyl-1,4-butanedioate

but-2-enedioic acid diethyl ester

Diethyl maleate

diethyl 2-ethoxysuccinate

Downstream raw materials:

3-cyclopropanecarbonyloxy-5-ethoxycarbonyl-2-cyclohexen-1-one

3-Acetoxy-5-oxo-cyclohex-3-enecarboxylic acid ethyl ester