1,6-Bis(4-methoxyphenyl)hexane-1,6-dione

Base Information

• Chemical Name: 1,6-Bis(4-methoxyphenyl)hexane-1,6-dione
• CAS No.: 4280-49-3
• Molecular Formula: C20H22 O4
• Molecular Weight: 326.392
• NSC Number: 22676
• DSSTox Substance ID: DTXSID70962707
• Nikkaji Number: J1.469.542G
• Mol file: 4280-49-3.mol

Synonyms:1,6-bis(4-methoxyphenyl)hexane-1,6-dione;4280-49-3;NSC22676;1,6-Bis(4-methoxyphenyl)-1,6-hexanedione;SCHEMBL3171960;DTXSID70962707;NSC-22676;STK527065;AKOS005460386

Chemical Property of 1,6-Bis(4-methoxyphenyl)hexane-1,6-dione

Chemical Property:

• Vapor Pressure: 3.7E-10mmHg at 25°C
• Boiling Point: 500.7°C at 760 mmHg
• Flash Point: 219.9°C
• Density: 1.108g/cm³
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 326.15180918
• Heavy Atom Count: 24
• Complexity: 352

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(=O)CCCCC(=O)C2=CC=C(C=C2)OC

Technology Process of 1,6-Bis(4-methoxyphenyl)hexane-1,6-dione

There total 25 articles about 1,6-Bis(4-methoxyphenyl)hexane-1,6-dione 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: 93.0%

methoxybenzene (100-66-3) + Adipic acid dichloride (111-50-2) → 1,6-bis(4-methoxyphenyl)hexa-1,6-dione (4280-49-3)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/jm9704917

Reference yield: 78.0%

1-(4-methoxyphenyl)cyclopropan-1-ol (15973-65-6) → 1,6-bis(4-methoxyphenyl)hexa-1,6-dione (4280-49-3)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate; In 2,2,2-trifluoroethanol; at 20 ℃; for 0.25h; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00967

Reference yield: 38.0%

cis-2-p-methoxybenzoyl-1-(p-methoxyphenyl)cyclopentanol → 1,6-bis(4-methoxyphenyl)hexa-1,6-dione (4280-49-3) + 1-(p-methoxybenzoyl)-2-(p-methoxyphenyl)cyclopentene (331969-54-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 97h;

DOI:10.1002/1099-0690(200101)2001:1<93::AID-EJOC93>3.0.CO;2-X

upstream raw materials:

1,2-bis(p-methoxyphenyl)cyclohexene

methoxybenzene

Adipic acid dichloride

1-bromo-4-methoxy-benzene

Downstream raw materials:

1,1,6,6-tetrakis-(4-methoxy-phenyl)-hexane-1,6-diol

(1E,2E)-3,8-bis(4-methoxyphenyl)-4,5,6,7-tetrahydro-1,2-diazocine

3,8-bis-(4-methoxy-phenyl)-octahydro-[1,2]diazocine

3,8-bis-(4-methoxy-phenyl)-3,4,5,6,7,8-hexahydro-[1,2]diazocine

Refernces

• 1、 Ghosh, Asit,Pati, Bedadyuti Vedvyas,Ravikumar, P. C.. "Rhodium-Catalyzed Room Temperature C-C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones". supporting information. . Retrieved 2020/04/02.
• 2、 Bietti, Massimo,Capone, Alberto. "One-electron oxidation of 2-(4-methoxyphenyl)-2-methylpropanoic and 1-(4-methoxyphenyl)cyclopropanecarboxylic acids in aqueous solution. The involvement of radical cations and the influence of structural effects and pH on the side-chain fragmentation reactivity". . p. 618 - 629. Retrieved 2008/09/18.