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| | Ethyl 2-oxocyclohexanecarboxylate Basic information |
| | Ethyl 2-oxocyclohexanecarboxylate Chemical Properties |
| | Ethyl 2-oxocyclohexanecarboxylate Usage And Synthesis |
| Chemical Properties | Clear colorless to pale yellow liquid | | Uses | Ethyl 2-Oxocyclohexanecarboxylate is used in biocatalysis. | | 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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| | Ethyl 2-oxocyclohexanecarboxylate Preparation Products And Raw materials |
| 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 |
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