4-Ethoxycarbonylbicyclo[2.2.2]octane-2,3-dicarboxylic acid

Base Information

• Chemical Name: 4-Ethoxycarbonylbicyclo[2.2.2]octane-2,3-dicarboxylic acid
• CAS No.: 3048-85-9
• Molecular Formula: C₁₃H₁₈O₆
• Molecular Weight: 270.282
• NSC Number: 177420
• DSSTox Substance ID: DTXSID90306543
• Mol file: 3048-85-9.mol

Synonyms:3048-85-9;NSC177420;4-ethoxycarbonylbicyclo[2.2.2]octane-2,3-dicarboxylic acid;DTXSID90306543;NSC-177420

Chemical Property of 4-Ethoxycarbonylbicyclo[2.2.2]octane-2,3-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 1.33E-09mmHg at 25°C
• Boiling Point: 456.5°Cat760mmHg
• Flash Point: 173.2°C
• Density: 1.376g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 270.11033829
• Heavy Atom Count: 19
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C12CCC(CC1)C(C2C(=O)O)C(=O)O

Technology Process of 4-Ethoxycarbonylbicyclo[2.2.2]octane-2,3-dicarboxylic acid

There total 5 articles about 4-Ethoxycarbonylbicyclo[2.2.2]octane-2,3-dicarboxylic acid 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:

ethyl 3,5-dioxo-4-oxatricyclo[5.2.2.02,6]undec-8-ene-1-carboxylate (105881-97-8) → 1-Aethoxycarbonyl-bicyclo<2.2.2>octan-2,3-dicarbonsaeure (3048-85-9)

Guidance literature:

Multistep reaction; (i) aq. KHCO₃, (ii) H₂, Pd-C;

DOI:10.1021/jo00829a010

Reference yield:

ethyl 2-(diethylamino)cyclohex-3-ene-1-carboxylate (129849-39-4) → 1-Aethoxycarbonyl-bicyclo<2.2.2>octan-2,3-dicarbonsaeure (3048-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid / 2 h / Reflux

2.1: 1 h / 100 - 170 °C

3.1: palladium on activated charcoal; hydrogen / ethyl acetate / 3 h

4.1: potassium carbonate / water / 2 h / Reflux

4.2: pH 1

With palladium on activated charcoal; hydrogen; potassium carbonate; acetic acid; In water; ethyl acetate;

DOI:10.1039/c8ob00205c

Reference yield:

ethyl 1,3-cyclohexadiene-1-carboxylate (3725-40-4) → 1-Aethoxycarbonyl-bicyclo<2.2.2>octan-2,3-dicarbonsaeure (3048-85-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1 h / 100 - 170 °C

2.1: palladium on activated charcoal; hydrogen / ethyl acetate / 3 h

3.1: potassium carbonate / water / 2 h / Reflux

3.2: pH 1

With palladium on activated charcoal; hydrogen; potassium carbonate; In water; ethyl acetate;

DOI:10.1039/c8ob00205c

upstream raw materials:

ethyl 3,5-dioxo-4-oxatricyclo[5.2.2.02,6]undec-8-ene-1-carboxylate

ethyl 2-(diethylamino)cyclohex-3-ene-1-carboxylate

ethyl 1,3-cyclohexadiene-1-carboxylate

(+/-)-bicyclo[2.2.2]octane-1,2r,3c-tricarboxylic acid-1-ethyl ester-2,3-anhydride

Downstream raw materials:

(bicyclo<2.2.2>oct-1-yl)methyl tosylate

bicyclo<2.2.2>octane-1-methanol

bicyclo[2.2.2]octane-1-carboxylic acid

Refernces