23733-68-8

Basic information

• Product Name: ()-3-(isopropyl)-6-methylcyclohex-2-en-1-one
• Synonyms: (1)-3-(Isopropyl)-6-methylcyclohex-2-en-1-one; 6-methyl-3-(propan-2-yl)cyclohex-2-en-1-one
• CAS NO: 23733-68-8
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.2334
• EINECS: 245-852-6
• Mol File: 23733-68-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 234.5°C at 760 mmHg
• Flash Point: 90.9°C
• Density: 0.915g/cm³
• Vapor Pressure: 0.0527mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: ()-3-(isopropyl)-6-methylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: ()-3-(isopropyl)-6-methylcyclohex-2-en-1-one(23733-68-8)
• EPA Substance Registry System: ()-3-(isopropyl)-6-methylcyclohex-2-en-1-one(23733-68-8)

Safety Data

• Hazardous Substances Data: 23733-68-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 6314, 1955 DOI: 10.1021/ja01628a072

Upstream product

• 64-18-6 formic acid 
• 3792-53-8 2-methyl-5-(prop-1-en-2-yl)cyclohexanone 
• 142472-68-2 p-menth-4-en-2-one 
• 29414-55-9 6,7-epoxymyrcene 
• 1195-92-2 (4R)-limonene 1,2-epoxide 
• 43205-82-9 carvotanacetone 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 29171-21-9 3,7-dimethyloct-6-en-1-yn-3-yl acetate 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 7152-15-0 ethyl 4-methyl-3-oxo-pentanoate 
• 408318-07-0 2,2-dichloro-bornane 
• 3212-36-0 2,6-dichloro-bornane 

Downstream Products

• 18069-17-5 2-methylglutaric acid 
• 500-00-5 3-p-menthene 
• 499-75-2 carvacrol 
• 99-87-6 4-methylisopropylbenzene 
• 74947-08-3 (+/-)-p-menth-3-en-2-one oxime 
• 4395-79-3 2-chloro-p-cymene 
• 499-69-4 (+/-)-menthol 
• 69770-96-3 4-Isobutyl-2-methyl-cyclopentanone 
• 121666-17-9 (2R,3S)-2,3-Dibromo-3-isopropyl-6-methyl-cyclohexanone 
• 43205-82-9 carvotanacetone 
• 618-45-1 3-isopropylhydroxybenzene 
• 95-48-7 ortho-cresol 
• 108-88-3 toluene 
• 121666-19-1 (2R,5S,6R)-2,5,6-Tribromo-5-isopropyl-2-methyl-cyclohexanone 

Relevant articles and documents

Advantageous heterogeneously catalysed hydrogenation of carvone with supercritical carbon dioxide

The hydrogenation of carvone was investigated for the first time in high-density carbon dioxide. The hydrogenation over 0.5 wt% Pd, or Rh, or Ru supported on alumina was found to be generally faster in a single supercritical (sc) phase (fluid reagents) than in a biphasic system (liquid + fluid reactants). The reaction with Pd produced fully hydrogenated products (isomers of carvomenthone) and carvacrol. The Rh catalyst was more selective and favoured carvomenthone isomers with higher selectivity and carvotanacetone as a secondary product. Additionally, the rhodium catalysed reaction exhibited high > 84% selectivity of carvotanacetone with the conversion of > 25% after only 2 min of reaction. The less active Ru catalyst gave significantly lower conversion and the product variety was greater as carvomenthone isomers, carvotanacetone and carvacrol were formed. The conversion and selectivity to carvomenthone within 2 h of the reaction starting followed the order: Pd > Rh > Ru and Rh > Pd > Ru, respectively. High conversion, and diverse and high selectivity accompanied by significant reduction in reaction time depending on the catalyst were achieved in supercritical CO2 compared with hydrogenation occurring in conventional organic solvents.

Unknown Camphor: Regioselective Rearrangement under Acylation in a CF3SO3H/(CF3CO)2O System

The utility of camphor in the chemical sciences is vast and well documented, yet the creation of camphor-derived potentially useful bicyclo[2.2.1]heptane scaffolds still remains one of the great challenges of synthetic organic chemistry. Herein, we show that CF3SO3H/(CF3CO)2O-mediated acylation of camphor with benzoic acids is accompanied by a cascade of alkyl and hydride shifts and opens access to a new type of polyfunctional isoborneol. In case of salicylic acids, camphor feels the presence of the ortho-hydroxy group in the aryl moiety, the influence of which provokes cleavage of the bicycloheptane skeleton to lead to monocyclic carvenone. The trifluoromethanesulfonic acid (TfOH)/trifluoroacetic anhydride (TFAA) mediated acylation of camphor with benzoic acids gives rise to a cascade of regioselective rearrangements of the bicycloheptane skeleton and allows the synthesis of a new type of previously unknown isoborneol. If salicylic acids are used as the acylating agents, the camphor is isomerized to give carvenone.

Heteropoly acid catalysis for the isomerization of biomass-derived limonene oxide and kinetic separation of the trans-isomer in green solvents

Terpenes are an abundant class of natural products, which is important for flavor and fragrance industry. Many acid catalyzed reactions used for upgrading terpenes still involve mineral acids as homogeneous catalysts and/or toxic solvents. Heteropoly acids represent a well-established eco-friendly alternative to conventional acid catalysts. As these reactions are usually performed in the liquid phase, solvents play a critical role for the process sustainability. In the present work, we developed a catalytic route to valuable fragrance ingredients, dihydrocarvone and carvenone, from limonene oxide by its isomerization using silica-supported tungstophosphoric acid as a heterogeneous catalyst and dialkylcarbonates as green solvents. The reaction pathway can be switched between dihydrocarvone and carvenone (obtained in 90% yield each) simply by changing the reaction temperature. In addition, we developed an efficient method for kinetic separation of trans-limonene oxide from commercial cis/trans-limonene oxide mixture and stereoselective synthesis of trans-dihydrocarvone.

Method for synthesizing carvacrol from dipentene dioxide

The invention discloses a method for synthesizing carvacrol from dipentene dioxide. The method comprises the following steps: step 1, utilizing the dipentene dioxide as a raw material and reducing thedipentene dioxide in a solvent A through a sodium borohydride water solution to obtain alpha,alpha,6-trimethyl-7-oxa bicyclo(4.1.0)heptane-3-methyl alcohol and 1,3,3-trimethyl-2-oxa bicyclo(2.2.2)octane-6-alcohol; step 2, dehydrating and rearranging the alpha,alpha,6-trimethyl-7-oxa bicyclo(4.1.0)heptane-3-methyl alcohol and 1,3,3-trimethyl-2-oxa bicyclo(2.2.2)octane-6-alcohol which are obtainedin step 1 through acid catalysis to obtain iso-dihydrocarvone; step 3, dissolving the iso-dihydrocarvone obtained in step 2 and a carbon-based compound catalyst into a solvent and heating the mixtureto generate dehydrogenation oxidation reaction, generating carvacrol, filtering the carvocrol to separate the carbon-based compound catalyst and performing reduced pressure rectification on filtrate to obtain a carvacrol finished product. The acid, the carbon-based compound catalyst and the solvent in the method disclosed by the invention all can be recycled, so that cost is reduced; the raw material of the dipentene dioxide in the method disclosed by the invention is an auxiliary product of the company, so that regeneration and comprehensive utilization of byproducts are achieved, and economic value of the byproducts is improved.

Method for synthetizing carvacrol through enediol

The invention discloses a method for synthetizing carvacrol through enediol. The method comprises the following steps of (1) dissolving the enediol and a catalyst A into a solvent, heating to enable the enediol to produce dehydration, ring-opening and rearrangement reactions, generating iso-dihydrocarvone, after reaction, neutralizing pH to be 7 to 8 through aqueous alkali, standing for layering, and carrying out organic phase vacuum distillation to obtain an iso-dihydrocarvone finished product; (2) dissolving the iso-dihydrocarvone prepared through the step (1) and a catalyst B into a solvent, heating to produce dehydrogenation oxidation reaction, generating the carvacrol, filtering and separating the catalyst B, carrying out filter liquor vacuum distillation to obtain a carvacrol finished product. According to the method for synthetizing the carvacrol through the enediol provided by the invention, the raw materials are convenient in source, low in price and easy to obtain; the synthetic process is green and environmentally friendly; post-processing purification only depends on rectification, so that the process is simple; the catalysts can be recycled so as to be suitable for industrial production.