2-hydroxy-4-methyl-2H-furan-5-one

Base Information

• Chemical Name: 2-hydroxy-4-methyl-2H-furan-5-one
• CAS No.: 931-23-7
• Molecular Formula: C5H6O3
• Molecular Weight: 114.101
• European Community (EC) Number: 951-427-2
• DSSTox Substance ID: DTXSID90415048
• Nikkaji Number: J919.478I
• Wikidata: Q82224173
• Mol file: 931-23-7.mol

Synonyms:931-23-7;5-hydroxy-3-methylfuran-2(5H)-one;2-hydroxy-4-methyl-2H-furan-5-one;5-hydroxy-3-methyl-2,5-dihydrofuran-2-one;5-hydroxy-3-methyl-2(5H)-furanone;2(5H)-Furanone, 5-hydroxy-3-methyl-;MFCD15145822;ghl.PD_Mitscher_leg0.903;SCHEMBL7548600;DTXSID90415048;4-Hydroxy-2-methylbut-2-enolide;CHEBI:195253;3-Methyl-5-hydroxyfuran-2(5H)-one;SY219275;CS-0139161;H1747;C77517;EN300-320927

Chemical Property of 2-hydroxy-4-methyl-2H-furan-5-one

Chemical Property:

• Melting Point: 72-73 °C
• Boiling Point: 90 °C(Press: 0.1 Torr)
• PKA: 10.03±0.40(Predicted)
• PSA: 46.53000
• Density: 1.349±0.06 g/cm3(Predicted)
• LogP: -0.19210
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 114.031694049
• Heavy Atom Count: 8
• Complexity: 148

Purity/Quality:

99%, ^*data from raw suppliers

Hydroxybutenolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(OC1=O)O
• Uses: Hydroxybutenolide can be used as reactant/reagent for synthetic preparation for enantioselective preparation of hydroxy-GR24 stereoisomers via contra-biomimetic nucleophilic cyclization.

Technology Process of 2-hydroxy-4-methyl-2H-furan-5-one

There total 2 articles about 2-hydroxy-4-methyl-2H-furan-5-one 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: 60.0%

citraconic acid anhydride (616-02-4) → 5-Hydroxy-3-methyl-5H-furan-2-one (931-23-7) + 5-hydroxy-4-methyl-5H-furan-2-one (40834-42-2)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -30 - -15 ℃; for 3h; Inert atmosphere;

DOI:10.1007/s00706-018-2179-x

Reference yield:

→ 5-Hydroxy-3-methyl-5H-furan-2-one (931-23-7) + 2-buten-4-olide (497-23-4)

Guidance literature:

Reference yield: 87.0%

5-Hydroxy-3-methyl-5H-furan-2-one (931-23-7) + thiophenol (108-98-5) → 3-methyl-5-(phenylthio)furan-2(5H)-one

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 80 ℃; for 15h;

DOI:10.1055/s-0037-1611462

upstream raw materials:

citraconic acid anhydride

Downstream raw materials:

2-chloro-4-methyl-2H-furan-5-one

C₁₀H₁₀O₅

2-methyl-4-(2-oxo-2,3,3a,6a-tetrahydro-4H-cyclopentafuran-3-ylidenemethoxy)but-2-en-4-olide

(R)-2-methylbutane-1,4-diol

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