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| | Methyl 2-oxocyclohexanecarboxylate Basic information |
| Product Name: | Methyl 2-oxocyclohexanecarboxylate | | Synonyms: | METHYL 2-OXOCYCLOHEXANECARBOXYLATE;METHYL CYCLOHEXANONE-2-CARBOXYLATE;AKOS 350;2-METHOXYCARBONYLCYCLOHEXANONE;2-OXO-CYCLOHEXANECARBOXYLIC ACID METHYL ESTER;2-oxo-cyclohexanecarboxylicacimethylester;Methyl 2-cyclohexanonecarboxylate;Methyl 2-oxo--1-cyclohexanecarboxylate | | CAS: | 41302-34-5 | | MF: | C8H12O3 | | MW: | 156.18 | | EINECS: | 255-306-9 | | Product Categories: | Achiral Oxygen | | Mol File: | 41302-34-5.mol |  |
| | Methyl 2-oxocyclohexanecarboxylate Chemical Properties |
| Boiling point | 50 °C/0.2 mmHg (lit.) | | density | 1.10 g/mL at 20 °C (lit.) | | refractive index | n20/D 1.483 | | Fp | 85 °C | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | form | Liquid | | pka | 12.04±0.20(Predicted) | | color | Clear colorless to slightly yellow | | BRN | 510258 | | InChI | InChI=1S/C8H12O3/c1-11-8(10)6-4-2-3-5-7(6)9/h6H,2-5H2,1H3 | | InChIKey | JEENWEAPRWGXSG-UHFFFAOYSA-N | | SMILES | C1(C(OC)=O)CCCCC1=O | | LogP | 0.290 (est) | | EPA Substance Registry System | Cyclohexanecarboxylic acid, 2-oxo-, methyl ester (41302-34-5) |
| Safety Statements | 23-24/25 | | RIDADR | NA 1993 / PGIII | | WGK Germany | 3 | | TSCA | TSCA listed | | HS Code | 29183000 | | Storage Class | 10 - Combustible liquids |
| | Methyl 2-oxocyclohexanecarboxylate Usage And Synthesis |
| Chemical Properties | clear colorless to slightly yellow liquid | | Uses | Methyl 2-Oxocyclohexanecarboxylate is a novel intermediate for the preparation of TRPA1 antagonists for treatment of pain and other TRPA1-associated diseases. | | Uses | Methyl 2-oxocyclohexanecarboxylate has been used in the synthesis of substituted tetrahydrobenzofuran derivatives via reaction with propargylic esters in the presence of palladium catalyst. | | Synthesis Reference(s) | Journal of the American Chemical Society, 102, p. 431, 1980 DOI: 10.1021/ja00521a100
Organic Syntheses, Coll. Vol. 7, p. 351, 1990 | | Synthesis | The flask is flushed with nitrogen and charged with 18.02 g (0.20 mol) of dimethyl carbonate, 50 mL of anhydrous tetrahydrofuran, and 6.12 g (0.25 mol) of sodium hydride. The suspension is stirred and heated to reflux temperature, at which time the slow, dropwise addition of 7.80 g (0.080 mol) of cyclohexanone in 20 mL of dry tetrahydrofuran is begun. After 2 min, 0.306 g (0.0076 mol) of powdered potassium hydride is added to initiate the reaction. The addition of cyclohexanone is continued over a 1-hr period. The mixture is stirred and heated at reflux for another 30 min, cooled in an ice bath for 15–20 min, and hydrolyzed by slowly adding 75 mL of 3 M aqueous acetic acid. The flask's contents are poured into 100 mL of aqueous sodium chloride, and the aqueous mixture is extracted with four 150-mL portions of chloroform. The organic layers are combined, dried with anhydrous sodium sulfate, and concentrated at room temperature with a rotary evaporator. Distillation of the residual liquid under reduced pressure gives 9.8–10.8 g (79–87%) of methyl 2-oxocyclohexanecarboxylate as a colorless liquid, bp 53–55°C.
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| | Methyl 2-oxocyclohexanecarboxylate Preparation Products And Raw materials |
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