5-Methyl-3-oxohexanoic acid methyl ester

Base Information

• Chemical Name: 5-Methyl-3-oxohexanoic acid methyl ester
• CAS No.: 30414-55-2
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Hs Code.: 2918300090
• UNII: 8HH8B3RXAQ
• DSSTox Substance ID: DTXSID50865540
• Nikkaji Number: J100.917F
• Wikidata: Q27270517
• Mol file: 30414-55-2.mol

Synonyms:Methyl5-methyl-3-oxohexanoate;Methyl 3-oxo-5-methylhexanoate;Methyl a-isovalerylacetate;Isovalerylaceticacid methyl ester;Methyl α-isovalerylacetate;

Chemical Property of 5-Methyl-3-oxohexanoic acid methyl ester

Chemical Property:

• Vapor Pressure: 0.342mmHg at 25°C
• Refractive Index: 1.419
• Boiling Point: 199.4 °C at 760 mmHg
• PKA: 10.40±0.46(Predicted)
• Flash Point: 75.7 °C
• PSA: 43.37000
• Density: 0.979 g/cm³
• LogP: 1.16470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl5-Methyl-3-oxohexanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)CC(=O)OC

Technology Process of 5-Methyl-3-oxohexanoic acid methyl ester

There total 16 articles about 5-Methyl-3-oxohexanoic acid methyl ester 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: 98.0%

4-methyl-2-pentanone (108-10-1) → methyl 5-methyl-3-oxohexanoate (30414-55-2)

Guidance literature:

carbonic acid dimethyl ester; With sodium hydride; In 1,4-dioxane; Heating / reflux;

4-methyl-2-pentanone; In 1,4-dioxane; for 3h; Heating / reflux;

With hydrogenchloride; In 1,4-dioxane; water; pH=7;

Reference yield: 95.0%

4-methyl-2-pentanone (108-10-1) + carbonic acid dimethyl ester (616-38-6) → methyl 5-methyl-3-oxohexanoate (30414-55-2)

Guidance literature:

With sodium hydride; In 1,4-dioxane; paraffin; for 2h; Heating;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<979::AID-EJOC979>3.0.CO;2-C

Reference yield: 68.0%

5-methyl-hex-2-enoic acid methyl ester (68797-67-1) → methyl 5-methyl-3-oxohexanoate (30414-55-2)

Guidance literature:

With tert.-butylhydroperoxide; sodium tetrachloropalladate(II); In acetic acid; tert-butyl alcohol; at 50 ℃; for 3h;

DOI:10.1246/cl.1980.257

upstream raw materials:

2-acetyl-5-methyl-3-oxo-hexanoic acid methyl ester

2-acetyl-5-methyl-3-oxo-hexanoic acid ethyl ester

sodium methylate

2-iodo-propane

Downstream raw materials:

(+/-)-4,8-dimethyl-6-oxo-nonanoic acid methyl ester

methyl (R)-5-methyl-3-hydroxypentanoate

4-(3-bromo-4-fluoro-phenyl)-2-isobutyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid methyl ester

(S)-methyl 5-methyl-3-acetamidohexanoate

Refernces

• 1、 Mitsudome, Takato,Yoshida, Syuhei,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi. "Highly atom-efficient oxidation of electron-deficient internal olefins to ketones using a palladium catalyst". . p. 5961 - 5964. Retrieved 2013/06/27.
• 2、 Davis, Jesse B.,Bailey, J. Daniel,Sello, Jason K.. "Biomimetic synthesis of a new class of bacterial signaling molecules". supporting information; experimental part. p. 2984 - 2987. Retrieved 2009/12/05.