Cyclohexanecarboxylic acid, 1-methyl-4-oxo-, ethyl ester

Uses

Ethyl 1-methyl-4-oxocyclohexanecarboxylate is a useful research chemical.

Synthesis

To a mixed solution of ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (7.3 g, 32.0 mmol) in acetonitrile (50 mL) and water (50 mL) was added cerium ammonium nitrate (CAN, 2.11 g, 3.85 mmol). The reaction mixture was heated to 70 °C and stirred for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and partitioned with ethyl acetate (50 mL) and water (50 mL). The aqueous layer was further extracted with ethyl acetate (50 mL x 2). The combined organic layers were washed with saturated brine (50 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford ethyl 1-methyl-4-oxocyclohexanoate (5 g, 85% yield) as a yellow oil, which was used directly in the subsequent reaction.

References

[1] Australian Journal of Chemistry, 1994, vol. 47, # 10, p. 1833 - 1841
[2] Patent: US2018/305320, 2018, A1. Location in patent: Paragraph 0228; 0231
[3] Patent: CN105566324, 2016, A. Location in patent: Paragraph 0337; 0341; 0342; 0343
[4] Patent: US2016/96841, 2016, A1. Location in patent: Paragraph 0333
[5] Patent: WO2011/2887, 2011, A1. Location in patent: Page/Page column 70-71