Dimethyl 3,6-dioxooctanedioate

Base Information

• Chemical Name: Dimethyl 3,6-dioxooctanedioate
• CAS No.: 58096-39-2
• Molecular Formula: C₁₀H₁₄O₆
• Molecular Weight: 230.218
• DSSTox Substance ID: DTXSID201297337
• Mol file: 58096-39-2.mol

Synonyms:dimethyl 3,6-dioxooctanedioate;58096-39-2;dimethyl 3,5-dioxooctanedionate;3,6-Dioxooctanedioic acid dimethyl ester;SCHEMBL11756126;DTXSID201297337;1,8-Dimethyl 3,6-dioxooctanedioate;AKOS032961278;3,6-dioxo-octanedioic acid dimethyl ester;A900119

Chemical Property of Dimethyl 3,6-dioxooctanedioate

Chemical Property:

• Boiling Point: 329.2±22.0 °C(Predicted)
• PKA: 10.00±0.46(Predicted)
• Density: 1.181±0.06 g/cm3(Predicted)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 230.07903816
• Heavy Atom Count: 16
• Complexity: 264

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CC(=O)CCC(=O)CC(=O)OC

Technology Process of Dimethyl 3,6-dioxooctanedioate

There total 2 articles about Dimethyl 3,6-dioxooctanedioate 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: 13.0%

4-butanolide (96-48-0) + 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1) → dimethyl 3,5-dioxooctanedionate (58096-39-2) + methyl <3-hydroxy-5-(3-hydroxypropyl)-2-methoxycarbonylphenyl>acetate (78133-91-2)

Guidance literature:

With titanium tetrachloride; In dichloromethane; 1.) -78 deg C, 2 h., 2.) room temp., overnight;

Reference yield:

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1) → dimethyl 3,5-dioxooctanedionate (58096-39-2) + acetoacetic acid methyl ester (105-45-3)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

Reference yield:

dimethyl 3,5-dioxooctanedionate (58096-39-2) → methyl jasmonate (1101843-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate; hydrogenchloride / water / pH 1 - Ca_.2

2: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C / 0 - 3000.3 Torr

3: caesium carbonate; tetrabutylammomium bromide / tert-butyl methyl ether / 0 - 20 °C / Inert atmosphere

4: water; lithium chloride / 120 - 130 °C

With hydrogenchloride; 5%-palladium/activated carbon; tetrabutylammomium bromide; water; hydrogen; sodium carbonate; caesium carbonate; lithium chloride; In methanol; tert-butyl methyl ether; water;

upstream raw materials:

4-butanolide

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

Downstream raw materials:

methyl jasmonate

(Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid