4-Carboxymethyl-3-methylbut-2-en-1,4-olide

Base Information

• Chemical Name: 4-Carboxymethyl-3-methylbut-2-en-1,4-olide
• CAS No.: 6307-98-8
• Molecular Formula: C14H11Cl3N2OS
• Molecular Weight: 156.138
• NSC Number: 48102,43335
• Nikkaji Number: J971.109K
• Wikidata: Q27102059
• Metabolomics Workbench ID: 50625
• Mol file: 6307-98-8.mol

Synonyms:3-methylmuconolactone;methylmuconolactone

Chemical Property of 4-Carboxymethyl-3-methylbut-2-en-1,4-olide

Chemical Property:

• Vapor Pressure: 7.07E-08mmHg at 25°C
• Boiling Point: 410.2°Cat760mmHg
• Flash Point: 178.6°C
• Density: 1.304g/cm³
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 156.04225873
• Heavy Atom Count: 11
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC1CC(=O)O

Technology Process of 4-Carboxymethyl-3-methylbut-2-en-1,4-olide

There total 12 articles about 4-Carboxymethyl-3-methylbut-2-en-1,4-olide 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: 71.0%

4-methyl-1,2-dihydroxybenzene (452-86-8) → 4-methyl-5-carboxymethyl-2-furanone (6307-98-8) + (2Z,4E)-3-methyl-2,4-hexadienedioic acid (31659-59-3)

Guidance literature:

With formic acid; Peroxyformic acid; ferrous ammonium sulphate hexahydrate; In water; for 22h; Green chemistry;

DOI:10.1039/d0gc02157a

Reference yield: 40.0%

p-cresol (106-44-5) → 4-methyl-5-carboxymethyl-2-furanone (6307-98-8) + 3-methyl-hexa-2t,4t-dienedioic acid (116672-65-2)

Guidance literature:

With 2,2'-dinitro-4,4'-di(trifluoromethyl)diphenyl diselenide; dihydrogen peroxide; In water; tert-butyl alcohol; at 80 ℃; for 20h; regioselective reaction;

DOI:10.1080/00397910802369687

Reference yield:

4-methyl-2-nitrophenol (119-33-5) → 4-methyl-5-carboxymethyl-2-furanone (6307-98-8)

Guidance literature:

With sulfuric acid; at 110 - 115 ℃;

upstream raw materials:

(2Z,4E)-3-methyl-2,4-hexadienedioic acid

4-methyl-2-nitrophenol

4-methyl-1,2-dihydroxybenzene

dihydrogen peroxide

Downstream raw materials:

rac-3-hydroxy-4-oxopentanoic acid

oxalic acid

(+/-)-4-Methylmuconolactone

Refernces

• 1、 Cain, Ronald B.,Freer, Andrew A.,Kirby, Gordon W.,Rao, Ghanokota V.. "Resolution of (+/-)-3-Methylmuconolactone and the Absolute Configurations of the Naturally Occurring 3- and 4-Methylmuconolactones: X-Ray Crystal Structures of (S)-1-Phenylethylammonium Salts and a Bromodilactone". . p. 202 - 203. Retrieved 1989.
• 2、 Giurg, Miroslaw,Kowal, Ewa,Muchalski, Hubert,Syper, Ludwik,Mlochowski, Jacek. "Catalytic oxidative domino degradation of alkyl phenols towards 2- and 3-substituted muconolactones". experimental part. p. 251 - 266. Retrieved 2009/04/07.
• 3、 McKague, A. Bruce. "Synthesis of muconic acids peracetic acid oxidation of catechols". . p. 1463 - 1475. Retrieved 2007/10/03.