| Identification | More | [Name]
Ethyl 2-oxocyclohexanecarboxylate | [CAS]
1655-07-8 | [Synonyms]
2-CARBETHOXYCYCLOHEXANONE
2-CYCLOHEXANONECARBOXYLIC ACID ETHYL ESTER
2-(ETHOXYCARBONYL)CYCLOHEXANONE
2-OXOCYCLOHEXANECARBOXYLIC ACID ETHYL ESTER
AKOS 91391
AKOS MSC-0386
CYCLOHEXANONE-2-CARBOXYLIC ACID ETHYL ESTER
CYCLOHEXANONE-A-CARBOXYLIC ACID ETHYL ESTER
ETHYL 2-CYCLOHEXANONECARBOXYLATE
ETHYL 2-OXOCYCLOHEXANECARBOXYLATE
ETHYL CYCLOHEXANONE-2-CARBOXYLATE
LABOTEST-BB LT00159541
2-oxo-cyclohexanecarboxylicaciethylester
Ethyl 1-oxo-2-cyclohexanecarboxylate
Ethyl 2-cyclohexanone-1-carboxylate
Ethyl 2-oxo-1-cyclohexanecarboxylate
Ethyl 2-oxocylohexanecarboxylate
Ethyl 2-oxylcyclohexanecarboxylic
2-Cyclohexanonecarboxylic acid ester
Ethyl cylcohexanecarboxylate | [EINECS(EC#)]
216-731-5 | [Molecular Formula]
C9H14O3 | [MDL Number]
MFCD00001631 | [Molecular Weight]
170.21 | [MOL File]
1655-07-8.mol |
| Questions And Answer | Back Directory | [Synthesis]
Diethyl carbonate (146 mL, 1.2 mol) and 150 mL of dry tetrahydrofuran were added to a 1000 mL three-necked flask. NaH (60%, 63 g, 1.6 mol) was added with stirring. After reflux for 1 h, a THF solution of cyclohexanone (50 mL, 0.48 mol) was added dropwise over approximately 0.5 h. After the addition was complete, reflux was continued for another 1.5 h. After cooling, the solution was adjusted to neutral with 3N hydrochloric acid, then poured into brine and extracted with dichloromethane (75 mL × 3). After drying the organic layer, vacuum distillation yielded a brown oily liquid (66 g, 80% yield), which was crude Ethyl 2-oxocyclohexanecarboxylate, and could be used directly in the next reaction. |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to pale yellow liquid | [Melting point ]
101 °C | [Boiling point ]
106 °C/11 mmHg (lit.) | [density ]
1.064 g/mL at 25 °C(lit.)
| [vapor pressure ]
8.7Pa at 25℃ | [refractive index ]
n20/D 1.477(lit.)
| [Fp ]
185 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Sparingly), Methanol (Sparingly) | [form ]
Oil | [pka]
12.06±0.20(Predicted) | [color ]
Colourless | [Water Solubility ]
Soluble in water. | [Detection Methods]
GC | [BRN ]
608356 | [InChI]
1S/C9H14O3/c1-2-12-9(11)7-5-3-4-6-8(7)10/h7H,2-6H2,1H3 | [InChIKey]
FGSGHBPKHFDJOP-UHFFFAOYSA-N | [SMILES]
CCOC(=O)C1CCCCC1=O | [LogP]
1.08 | [CAS DataBase Reference]
1655-07-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Cyclohexanecarboxylic acid, 2-oxo-, ethyl ester(1655-07-8) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
1655-07-8(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H227 | [Precautionary statements ]
P210-P280-P370+P378-P403+P235-P501 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
IRRITANT | [HS Code ]
29183000 | [Storage Class]
10 - Combustible liquids |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Tetrahydrofuran-->Toluene-->Sodium hydride-->Diethyl oxalate-->Sodium ethoxide-->Cyclohexanone-->Diethyl carbonate-->Potassium ethylate | [Preparation Products]
3-Methoxycyclohexene-->6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one-->2-Hydroxycyclohexanecarboxylic acid-->1,2-Cyclopentanedicarboxylic acid-->11-oxo-5,7,8,9,10,11-hexahydrobenzo[4,5]imidazo[1,2-b]isoquinoline-6-carbonitrile-->4,5,6,7-Tetrahydro-2H-indazol-3(3aH)-one |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to pale yellow liquid | [Uses]
Ethyl 2-oxocyclohexanecarboxylate is used to produce other chemicals. For example, it can react with 4-methyl-aniline to get 2-oxo-cyclohexanecarboxylic acid p-toluidide. The reaction occurs with reagent DMAP | [Reactions]
The reaction of ethyl 2-oxo cyclohexane carboxylate (I) with phenyl vinyl sulphoxide (II) and sodium hydride followed by pyrolysis of the resulting phenyl sulphonyl ethyl compound (III) gives the 1-vinyl compound (IV).
Baeyer-Villiger oxidation of methyl 3- and 4-oxocyclohexanecarboxylates gave the expected hexanolides, whereas ethyl 2-oxocyclohexanecarboxylate(I) gave 5-ethoxyoxalylpentanoic acid by way of ethyl 1-hydroxy-2-oxocyclohexanecarboxylate, formed by epoxidation of the enol form of (I)[1-2].
| [Synthesis Reference(s)]
Canadian Journal of Chemistry, 42, p. 1333, 1964 DOI: 10.1139/v64-205
The Journal of Organic Chemistry, 53, p. 878, 1988 DOI: 10.1021/jo00239a038
Tetrahedron Letters, 7, p. 2201, 1966 | [References]
[1] A. Hubert, P. S. Starcher. “The Baeyer-Villiger oxidation of alkyl oxocyclohexanecarboxylates.” Journal of The Chemical Society C: Organic 377 1 (1968): 2500–2502.
[2] G. Koppel, M. D. Kinnick. “Phenyl vinyl sulphoxide, a vinyl carbonium ion synthetic equivalent.” Journal of The Chemical Society, Chemical Communications 27 1 (1975): 473–473.
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