3-Methylbutyrolactone

Base Information

• Chemical Name: 3-Methylbutyrolactone
• CAS No.: 1679-49-8
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.117
• European Community (EC) Number: 264-725-6,839-297-4
• NSC Number: 134770
• DSSTox Substance ID: DTXSID70862733
• Nikkaji Number: J141.092J
• Wikidata: Q81986285
• Metabolomics Workbench ID: 38053
• Mol file: 1679-49-8.mol

Synonyms:3-methylbutyrolactone

Chemical Property of 3-Methylbutyrolactone

Chemical Property:

• Vapor Pressure: 0.235mmHg at 25°C
• Refractive Index: 1.43
• Boiling Point: 206.624 °C at 760 mmHg
• Flash Point: 74.98 °C
• PSA: 26.30000
• Density: 1.04 g/cm³
• LogP: 0.56940
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 88.1

Purity/Quality:

99%, ^*data from raw suppliers

Dihydro-4-methyl-2(3H)-furanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)OC1
• Uses: Dihydro-4-methyl-2(3H)-furanone (cas# 1679-49-8) was identified as an aroma contributing compound in a flavour profiling of Wild Harenna coffee beans.

Technology Process of 3-Methylbutyrolactone

There total 75 articles about 3-Methylbutyrolactone 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: 100.0%

4-methyl-2(5H)-furanone (6124-79-4) → dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; under 1500.15 Torr;

DOI:10.1002/chem.201104073

Reference yield: 93.0%

2-Butoxy-4-methyl-tetrahydrofuran (82918-74-9) → dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8)

Guidance literature:

With Jones-reagent; In acetone; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)81285-0

Reference yield: 87.0%

Dimethyl itakonate (617-52-7) → 3-methyltetrahydrofuran (13423-15-9) + dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8) + 3-methyltetrahydro-2-furanone (1679-47-6)

Guidance literature:

With C₅₇H₆₉P₃Ru; hydrogen; bis(trifluoromethanesulfonyl)amide; at 200 ℃; for 0.0833333h; under 75007.5 Torr; Autoclave;

upstream raw materials:

4,5-dimethylfuran-2-(3H)-one

3-methyltetrahydrofuran

2-Butoxy-4-methyl-tetrahydrofuran

3-methylbutyric acid

Downstream raw materials:

3-methyl glutaric acid

2-methyl-4-oxo-5-(phenylthio)pentanol

2-methylbutanedioic acid

(2R,3R)-2-Acetyl-2-hydroxy-3-methyl-γ-butyrolactone

Refernces

• 1、 Krohn, Karsten,Riaz, Muhammad,Floerke, Ulrich. "Synthesis of xyloketals, natural products from the mangrove fungus Xylaria sp.". . p. 1261 - 1270. Retrieved 2004.
• 2、 Ziegler, Frederick E.,Thottathil, John K.. "HIGH DIASTEREOSELECTION IN THE CLAISEN REARRANGEMENT OF ENANTIOMERICALLY PURE BUTYROLACTONES". . p. 3531 - 3534. Retrieved 1982.
• 3、 Gowda, Ravikumar R.,Chen, Eugene Y.-X.. "Regioselective Hydrogenation of Itaconic Acid to Γ-Isovalerolactone by Transition-Metal Nanoparticle Catalysts". . p. 973 - 977. Retrieved 2019/02/06.
• 4、 -. "METHODS OF FORMING DIOL COMPOUNDS". Paragraph 0115. . Retrieved 2017/11/06.