Diethyl cyclohexa-3,5-diene-1,2-dicarboxylate

Base Information

• Chemical Name: Diethyl cyclohexa-3,5-diene-1,2-dicarboxylate
• CAS No.: 6268-45-7
• Molecular Formula: C12H16 O4
• Molecular Weight: 224.257
• NSC Number: 36261
• DSSTox Substance ID: DTXSID80284220
• Mol file: 6268-45-7.mol

Synonyms:6268-45-7;diethyl cyclohexa-3,5-diene-1,2-dicarboxylate;NSC36261;dihydrodiethyl phthalate;SCHEMBL6316661;DTXSID80284220;NSC-36261

Chemical Property of Diethyl cyclohexa-3,5-diene-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.00115mmHg at 25°C
• Boiling Point: 300°Cat760mmHg
• Flash Point: 143.1°C
• Density: 1.114g/cm³
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 224.10485899
• Heavy Atom Count: 16
• Complexity: 285

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C=CC=CC1C(=O)OCC

Technology Process of Diethyl cyclohexa-3,5-diene-1,2-dicarboxylate

There total 2 articles about Diethyl cyclohexa-3,5-diene-1,2-dicarboxylate 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:

benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) → 3,5-cyclohexadiene-1,2-trans-dicarboxylic acid (22919-28-4) + cyclohexa-3,5-diene-1,2-dicarboxylic acid diethyl ester (6268-45-7)

Guidance literature:

With sulfuric acid; bei der elektrolytischen Reduktion;

Reference yield:

ethanol (64-17-5) + trans-cyclohexa-3,5-diene-1,2-dicarboxylic acid (5675-13-8,22919-28-4,26554-23-4) → trans 1,2-Dicarbethoxy-cyclohexa-3,5-dien (6268-45-7,32515-61-0,77803-86-2)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1016/S0040-4020(01)90879-8

Reference yield:

trans 1,2-Dicarbethoxy-cyclohexa-3,5-dien (6268-45-7,32515-61-0,77803-86-2) → 8,9-Dimethylen-4-phenyl-2,4,6-triazatricyclo<5.2.2.02,6>undecan-3,5-dion (86814-93-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / LiAlH₄ / diethyl ether / Heating

2: 81 percent / acetone

3: 78 percent / H₂ / 5percent Pd-C / methanol / Ambient temperature

4: 71 percent / pyridine / 0 °C

5: 67 percent / KOtBu / dimethylsulfoxide / 0.08 h / Ambient temperature

With lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; palladium on activated charcoal; In pyridine; methanol; diethyl ether; dimethyl sulfoxide; acetone;

upstream raw materials:

benzene-1,2-dicarboxylic acid

ethanol

trans-cyclohexa-3,5-diene-1,2-dicarboxylic acid

Downstream raw materials:

10,11-Dimethylen-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5-dion

8,9-Dimethylen-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undecan-3,5-dion

(8R*,9R*)-8,9-Bis(hydroxymethyl)-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undecan-3,5-dion

(10R*,11R*)-10,11-Bis(hydroxymethyl)-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5-dion