2-[(4-Methylphenyl)methyl]cyclohexanone

Base Information

• Chemical Name: 2-[(4-Methylphenyl)methyl]cyclohexanone
• CAS No.: 62596-28-5
• Molecular Formula: C14H18O
• Molecular Weight: 202.296
• DSSTox Substance ID: DTXSID101281080
• Nikkaji Number: J2.790.864K
• Mol file: 62596-28-5.mol

Synonyms:SCHEMBL7623394;DTXSID101281080;AKOS010640834;2-[(4-Methylphenyl)methyl]cyclohexanone;62596-28-5

Chemical Property of 2-[(4-Methylphenyl)methyl]cyclohexanone

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 202.135765193
• Heavy Atom Count: 15
• Complexity: 213

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)CC2CCCCC2=O

Technology Process of 2-[(4-Methylphenyl)methyl]cyclohexanone

There total 6 articles about 2-[(4-Methylphenyl)methyl]cyclohexanone 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: 87.0%

4-Methylbenzyl alcohol (589-18-4) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (+/-)-2-(4-methylbenzyl)cyclohexanone (62596-28-5)

Guidance literature:

With C₅₁H₃₉As₂N₃O₂RuS; sodium hydroxide; In toluene; at 105 ℃; for 8h;

DOI:10.1016/j.ica.2020.119887

Reference yield: 77.0%

2-(4-methylbenzyl)cyclohexanone O-methyl oxime → (+/-)-2-(4-methylbenzyl)cyclohexanone (62596-28-5)

Guidance literature:

With hydrogenchloride; formaldehyd; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1039/c5sc03903g

Reference yield:

2-methylcyclohexanone O-methyl oxime (39209-07-9) + bis(4-methylphenyl)iodonium trifluoromethanesulfonate (123726-16-9) → (+/-)-2-(4-methylbenzyl)cyclohexanone (62596-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: silver carbonate; Trimethylacetic acid; palladium diacetate / 1,2-dichloro-ethane / 5 h / 85 °C

2: formaldehyd; hydrogenchloride / tetrahydrofuran / 5 h / 20 °C

With hydrogenchloride; formaldehyd; palladium diacetate; silver carbonate; Trimethylacetic acid; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1039/c5sc03903g

upstream raw materials:

cyclohexanone

4-Methylbenzyl chloride

2-methylcyclohexanone O-methyl oxime

bis(4-methylphenyl)iodonium trifluoromethanesulfonate

Downstream raw materials:

2-(2,2-Dimethoxy-acetyl)-6-(4-methyl-benzyl)-cyclohexanone

(E)-3-[2-(4-Fluoro-phenyl)-7-(4-methyl-benzyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-propenal

Refernces

• 1、 Albright, Haley,Riehl, Paul S.,McAtee, Christopher C.,Reid, Jolene P.,Ludwig, Jacob R.,Karp, Lindsey A.,Zimmerman, Paul M.,Sigman, Matthew S.,Schindler, Corinna S.. "Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) Homo-Dimers as Lewis Acidic Superelectrophiles". supporting information. p. 1690 - 1700. Retrieved 2019/01/26.