5-hydroxy-4,5-diphenylfuran-2(5H)-one

Base Information

• Chemical Name: 5-hydroxy-4,5-diphenylfuran-2(5H)-one
• CAS No.: 86071-41-2
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.269
• Mol file: 86071-41-2.mol

Synonyms:Crotonicacid, 4,4-dihydroxy-3,4-diphenyl-, cis-, g-lactone (5CI); NSC 155183

Chemical Property of 5-hydroxy-4,5-diphenylfuran-2(5H)-one

Chemical Property:

• Vapor Pressure: 8.73E-10mmHg at 25°C
• Boiling Point: 473.9°C at 760 mmHg
• Flash Point: 207.6°C
• Density: 1.318g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-hydroxy-4,5-diphenylfuran-2(5H)-one

There total 4 articles about 5-hydroxy-4,5-diphenylfuran-2(5H)-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:

methyl-(Z)-3-phenyl-3-(tosyloxy) acrylate → 3,4-diphenyl-4-oxo-2-butenoic acid (55340-26-6) + 5-hydroxy-4,5-diphenylfuran-2(5H)-one (86071-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate; palladium(II) trifluoroacetate; tricyclohexylphosphine / toluene / 16 h / 100 °C / Inert atmosphere

2.1: potassium hydroxide / tetrahydrofuran; water / 2 h / 20 °C

2.2: 16 h / 20 °C

With palladium(II) trifluoroacetate; potassium carbonate; potassium hydroxide; tricyclohexylphosphine; In tetrahydrofuran; water; toluene; 1.1: |Suzuki-Miyaura Coupling;

DOI:10.1002/ejoc.201900023

Reference yield:

methyl 3-oxo-3-phenylpropionate (614-27-7) → 3,4-diphenyl-4-oxo-2-butenoic acid (55340-26-6) + 5-hydroxy-4,5-diphenylfuran-2(5H)-one (86071-41-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 16 h / 0 - 20 °C

2.1: potassium carbonate; palladium(II) trifluoroacetate; tricyclohexylphosphine / toluene / 16 h / 100 °C / Inert atmosphere

3.1: potassium hydroxide / tetrahydrofuran; water / 2 h / 20 °C

3.2: 16 h / 20 °C

With palladium(II) trifluoroacetate; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; lithium chloride; potassium hydroxide; tricyclohexylphosphine; In tetrahydrofuran; water; toluene; acetonitrile; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1002/ejoc.201900023

Reference yield:

acetophenone (98-86-2) → 3,4-diphenyl-4-oxo-2-butenoic acid (55340-26-6) + 5-hydroxy-4,5-diphenylfuran-2(5H)-one (86071-41-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / toluene; mineral oil / 0.5 h / 115 °C

1.2: 1 h / 115 °C

2.1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 16 h / 0 - 20 °C

3.1: potassium carbonate; palladium(II) trifluoroacetate; tricyclohexylphosphine / toluene / 16 h / 100 °C / Inert atmosphere

4.1: potassium hydroxide / tetrahydrofuran; water / 2 h / 20 °C

4.2: 16 h / 20 °C

With palladium(II) trifluoroacetate; N,N,N,N,-tetramethylethylenediamine; sodium hydride; potassium carbonate; lithium chloride; potassium hydroxide; tricyclohexylphosphine; In tetrahydrofuran; water; toluene; acetonitrile; mineral oil; 3.1: |Suzuki-Miyaura Coupling;

DOI:10.1002/ejoc.201900023

upstream raw materials:

methyl 3-oxo-3-phenylpropionate

acetophenone

(Z)-methyl 4-oxo-3,4-diphenylbut-2-enoate