3-(3-Phenylpropyl)-4-hydroxy-2(5H)furanone

Base Information

• Chemical Name: 3-(3-Phenylpropyl)-4-hydroxy-2(5H)furanone
• CAS No.: 78128-85-5
• Molecular Formula: C13H14 O3
• Molecular Weight: 218.27
• Mol file: 78128-85-5.mol

Synonyms:Valericacid, 2-(1,2-dihydroxyethylidene)-5-phenyl-, g-lactone (6CI)

Chemical Property of 3-(3-Phenylpropyl)-4-hydroxy-2(5H)furanone

Chemical Property:

• Vapor Pressure: 2.77E-06mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• Boiling Point: 374.8°C at 760 mmHg
• Flash Point: 144.1°C
• PSA: 46.53000
• Density: 1.23g/cm³
• LogP: 2.37820

Purity/Quality:

99% ^*data from raw suppliers

3-(3-PHENYLPROPYL)-4-HYDROXY-2(5H)FURANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(3-Phenylpropyl)-4-hydroxy-2(5H)furanone

There total 2 articles about 3-(3-Phenylpropyl)-4-hydroxy-2(5H)furanone 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:

4-hydroxy-3-(1-oxo-3-phenylpropyl)-2(5H)-furanone (145436-97-1) → 4-hydroxy-3-(3-phenylpropyl)furan-2(5H)-one (78128-85-5)

Guidance literature:

With sodium cyanoborohydride; In acetic acid; at 10 - 25 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201100491

Reference yield:

3-Phenylpropionic acid (501-52-0) → 4-hydroxy-3-(3-phenylpropyl)furan-2(5H)-one (78128-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide / dichloromethane / 0 - 25 °C / Inert atmosphere

2: sodium cyanoborohydride / acetic acid / 10 - 25 °C / Inert atmosphere

With dmap; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; acetic acid; 1: Fries rearrangement;

DOI:10.1002/ejoc.201100491

Reference yield: 74.0%

trifluoromethylsulfonic anhydride (358-23-6) + 4-hydroxy-3-(3-phenylpropyl)furan-2(5H)-one (78128-85-5) → 5-oxo-4-(3-phenylpropyl)-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (1316228-85-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201100491

upstream raw materials:

4-hydroxy-3-(1-oxo-3-phenylpropyl)-2(5H)-furanone

3-Phenylpropionic acid

Downstream raw materials:

3-(3-phenylpropyl)-2,5-dihydrofuran-2-one

5-oxo-4-(3-phenylpropyl)-2,5-dihydrofuran-3-yl trifluoromethanesulfonate

Refernces