2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

Base Information

• Chemical Name: 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
• CAS No.: 159853-36-8
• Molecular Formula: C20H14O3
• Molecular Weight: 302.32300
• DSSTox Substance ID: DTXSID10348561
• Nikkaji Number: J1.405.987C
• Wikidata: Q82123499
• Metabolomics Workbench ID: 49370
• Mol file: 159853-36-8.mol

Synonyms:4'-O-Methylirenolone;159853-36-8;2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one;2-hydroxy-4-(4-methoxyphenyl)phenalen-1-one;1H-phenalen-1-one, 2-hydroxy-4-(4-methoxyphenyl)-;DTXSID10348561;AKOS032949146;2-hydroxy-4-(4'-methoxyphenyl)-1h-phenalen-1-one;2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalene-1-one

Chemical Property of 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

Chemical Property:

• PSA: 46.53000
• LogP: 4.61060
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 302.094294304
• Heavy Atom Count: 23
• Complexity: 489

Purity/Quality:

99.90% ^*data from raw suppliers

4'-O-Methylirenolone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=C3C=C(C(=O)C4=CC=CC(=C43)C=C2)O

Technology Process of 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

There total 7 articles about 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-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: 100.0%

cis-2,3-dihydroxy-4-(p-hydroxyphenyl)-phenalen-1-one → 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one (159853-36-8)

Guidance literature:

With sulfuric acid; In acetone; for 1h;

DOI:10.1016/S0040-4020(01)85707-0

Reference yield:

3-(4-Methoxy-phenyl)-3b,4a-dihydro-4-oxa-cyclopropa[a]phenalen-5-one (159853-35-7) → 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one (159853-36-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 2h;

DOI:10.1016/S0040-4020(01)85707-0

Reference yield:

Perinaphthenon (548-39-0) → 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one (159853-36-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) 2,3-dichloro-5,6-dicyano-p-benzoquinone / 1.) ether, reflux, 3 h, 2.) CH₂Cl₂, reflux, 3 h

2: 1.) DIBAH, 2.) Jones reagent / 1.) toluene, -78 deg C, 4 h, 2.) acetone, room temp., 15 min

3: 70percent t-butyl-hydroperoxide, 40percent benzyltrimethylammonium hydroxide / benzene / Ambient temperature

4: p-toluenesulfonic acid / CH₂Cl₂ / 2 h

With tert.-butylhydroperoxide; jones reagent; N-benzyl-trimethylammonium hydroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)85707-0

upstream raw materials:

3-(4-Methoxy-phenyl)-3b,4a-dihydro-4-oxa-cyclopropa[a]phenalen-5-one

Perinaphthenon

9-(4-methoxyphenyl)-1H-phenalen-1-one

4-methoxyphenyl magnesium bromide

Downstream raw materials:

irenolone