3,3-Dimethylcyclohexyl methyl ketone

Base Information

• Chemical Name: 3,3-Dimethylcyclohexyl methyl ketone
• CAS No.: 25304-14-7
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 2914299000
• European Community (EC) Number: 246-799-1
• UNII: MH1R8F7762
• DSSTox Substance ID: DTXSID2051924
• Nikkaji Number: J236.121C
• Wikidata: Q27284021
• Mol file: 25304-14-7.mol

Synonyms:1-(3,3-dimethylcyclohexyl)ethan-1-one

Chemical Property of 3,3-Dimethylcyclohexyl methyl ketone

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 0.287mmHg at 25°C
• Refractive Index: 1.437
• Boiling Point: 202.8 °C at 760 mmHg
• Flash Point: 82 °C
• PSA: 17.07000
• Density: 0.875 g/cm³
• LogP: 2.79180
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCCC(C1)(C)C

Technology Process of 3,3-Dimethylcyclohexyl methyl ketone

There total 13 articles about 3,3-Dimethylcyclohexyl methyl ketone 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: 74.0%

5,5-dimethyl-8-p-toluenesulfonyloxyoctan-2-one (316378-01-5) → 1-(3,3-dimethyl-cyclohexyl)-ethanone (25304-14-7)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 80 ℃; for 8h;

DOI:10.1055/s-2004-829115

Reference yield:

alpha,3,3-trimethylcyclohexanemethanol (25225-09-6) + 2,6,6-trimethyl-cycloheptanol (33515-82-1) → 1-(3,3-dimethyl-cyclohexyl)-ethanone (25304-14-7) + 3,3,7-trimethylcycloheptanone (4436-59-3)

Guidance literature:

at 70 - 85 ℃; under 1 Torr; Overall yield = 96 %; Overall yield = 285 g;

Reference yield:

3-chloro-5,5-dimethylcyclohex-2-en-1-one (17530-69-7) → 1-(3,3-dimethyl-cyclohexyl)-ethanone (25304-14-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 5percent palladium on charcoal

2: 1.) PCl₅, 2.) NaOEt / 2.) reflux, 19 h

3: 69 percent / Na

4: 50 percent / AlCl₃ / CH₂Cl₂ / 6.25 h / 0 °C

5: H₂ / 5percent Pd-C / ethanol

With aluminium trichloride; phosphorus pentachloride; hydrogen; sodium ethanolate; sodium; palladium on activated charcoal; In ethanol; dichloromethane;

upstream raw materials:

1-(5,5-dimethyl-cyclohexa-1,3-dienyl)-ethanone

3-acetyl-5,5-dimethylcyclohexene

1-(5',5'-dimethylcyclohex-1'-enyl)ethanone

5,5-dimethyl-8-p-toluenesulfonyloxyoctan-2-one

Downstream raw materials:

3,3-dimethyl-1-(2-propenyl)-1-acetylcyclohexane

1-acetyl-1-methallyl-3,3-dimethylcyclohexane

1-(3,3-dimethyl-cyclohexyl)-pent-4-en-1-one

(-)-(1R,1'S)-1-(3',3'-dimethyl-1'-cyclohexyl)-1-ethanol

Refernces

• 1、 -. "Optically Active Ester Compounds and their use in Perfume Compositions". Page/Page column 7-8. . Retrieved 2009/12/05.
• 2、 Petrovic, Goran,Cekovic, Zivorad. "[4+2] Cyclohexane ring formation by a tandem of a free radical alkylation of a non-activated δ-carbon atom and intramolecular carbanion cycloalkylation". . p. 1671 - 1679. Retrieved 2007/10/03.