3-(4-Hydroxybenzylidene)dihydro-2(3H)-furanone

Base Information

• Chemical Name: 3-(4-Hydroxybenzylidene)dihydro-2(3H)-furanone
• CAS No.: 4736-30-5
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.199
• NSC Number: 16873
• Nikkaji Number: J2.408.224E
• ChEMBL ID: CHEMBL3189445
• Mol file: 4736-30-5.mol

Synonyms:3-(4-Hydroxybenzylidene)dihydro-2(3H)-furanone;4736-30-5;NSC16873;NSC 16873;(3E)-3-[(4-hydroxyphenyl)methylidene]oxolan-2-one;MLS000737817;CHEMBL3189445;HMS2882L11;NSC-16873;NCGC00246759-01;SMR000528173;(3E)-3-(4-Hydroxybenzylidene)tetrahydrofuran-2-one;(3E)-3-[(4-hydroxyphenyl)methylene]tetrahydrofuran-2-one

Chemical Property of 3-(4-Hydroxybenzylidene)dihydro-2(3H)-furanone

Chemical Property:

• Vapor Pressure: 9.42E-08mmHg at 25°C
• Boiling Point: 423°C at 760 mmHg
• Flash Point: 194.1°C
• Density: 1.335g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 190.062994177
• Heavy Atom Count: 14
• Complexity: 249

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC(=O)C1=CC2=CC=C(C=C2)O
• Isomeric SMILES: C\1COC(=O)/C1=C/C2=CC=C(C=C2)O

Technology Process of 3-(4-Hydroxybenzylidene)dihydro-2(3H)-furanone

There total 7 articles about 3-(4-Hydroxybenzylidene)dihydro-2(3H)-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: 1.8%

4-butanolide (96-48-0) + benzaldehyde (100-52-7) → 3-((Ξ)-4-hydroxy-benzylidene)-dihydro-furan-2-one (4736-30-5)

Guidance literature:

With sodium methylate; In toluene; at 40 - 50 ℃; for 1h;

DOI:10.1248/cpb.34.121

Reference yield:

α-methylene-γ-butyrolactone (547-65-9) + 4-hydroxybenzenediazonium tetrafluoroborate → (E)-3-(4-hydroxybenzylidene)dihydrofuran-2(3H)-one (4736-30-5,102271-69-2) + 3-(4-hydroxybenzyl)furan-2(5H)-one

Guidance literature:

With palladium diacetate; In methanol; at 20 ℃; for 12h; Overall yield = 76 %; Overall yield = 58 mg; Inert atmosphere;

DOI:10.1021/acs.joc.6b02207

Reference yield:

α-(4-Benzyloxybenzyliden)-butyrolacton (73839-66-4) → 3-((Ξ)-4-hydroxy-benzylidene)-dihydro-furan-2-one (4736-30-5)

Guidance literature:

With hydrogenchloride; acetic acid;

DOI:10.1021/jo01083a009

upstream raw materials:

4-butanolide

4-hydroxy-benzaldehyde

α-(4-Benzyloxybenzyliden)-butyrolacton

benzaldehyde

Downstream raw materials:

3-(4-hydroxybenzyl)dihydrofuren-2(3H)-one

α-(4-Acetoxybenzyliden)-butyrolacton

Refernces

• 1、 Katsumi,Kondo,Yamashita,Hidaka,Hosoe,Watanabe. "Studies on styrene derivatives. I. Synthesis and antiinflammatory activities of α-benzylidene-γ-butyrolactone derivatives". . p. 121 - 129. Retrieved 2007/10/02.