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

Flash point:

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 Information

Safety Statements 

23-24/25

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

29183000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Methyl 2-oxocyclohexanecarboxylate Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

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.

Uses

Methyl 2-Oxocyclohexanecarboxylate is a novel intermediate for the preparation of TRPA1 antagonists for treatment of pain and other TRPA1-associated diseases.

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.

Methyl 2-oxocyclohexanecarboxylate(41302-34-5)Related Product Information

• 3,4-Epoxycyclohexane carboxylic acid, methyl ester
• Diethyl succinosuccinate
• DIETHYL 2,5-DIOXOBICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLATE
• 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester
• Ethyl 2-oxocyclohexanecarboxylate
• 2-METHOXYCARBONYLCYCLOHEXANONE
• 6-CARBETHOXY-2,2,6-TRIMETHYLCYCLOHEXANONE
• ETHYL 4-METHYL-2-CYCLOHEXANONE-1-CARBOXYLATE
• METHYL 2,2-DIMETHYL-4,6-DIOXOCYCLOHEXANECARBOXYLATE, 97
• AKOS BB-2935
• AKOS BC-1751
• (+)-CAMPHORCARBOXYLIC ACID ETHYL ESTER
• methyl 5-[(2-hydroxyanilino)methylene]-2,2-dimethyl-4,6-dioxocyclohexanecarboxylate
• ETHYL (-)-CAMPHORCARBOXYLATE
• AKOS BB-2936
• SPECS AG-690/11765511
• AURORA KA-6600
• AKOS B024701