2-propylcyclohexan-1-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of commercially available 1-cyclohex-1-enylpyrrolidine 1(5 g, 99.2 mmol) and propyl bromide (36 mL, 4 eq) in benzene was refluxed at 90° C. for overnight. Another 4 eq of propyl bromide (36 mL) was added and refluxing was continued for overnight. The reaction mixture was cooled to room temperature. 30 mL of water was added, and the resulting solution refluxed for 1 hour. After cooling to room temperature, 30 mL of 1M H2SO4 was added and the solution stirred for 10 minutes. The mixture was extracted with ether, and the combined organic extracts were washed with NaHCO3, H2O, brine, and dried over MgSO4. Purification by column chromatography using EtOAc/hex (1:3) as eluant afforded 2.12 g (15.3%) of 2-propylcyclohexanone. Spectroscopic data: 1H NMR (CDCl3, 300 MHz) δ=0.90 (t, 3H, J=7.035 Hz), 1.14-1.45 (m, 5H), 1.63-1.88 (m, 4H), 1.99-2.14 (m, 2H), 2.23-2.42 (m, 2H). refluxing the resulting solution refluxed for 1 hour After cooling to room temperature The mixture was extracted with ether the combined organic extracts were washed with NaHCO3, H2O, brine dried over MgSO4 Purification by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: in the same manner but replacing 2-methylcyclohexanone with an equivalent amount of 2-ethylcyclohexanone or 2-propylcyclohexanone, 1-ethyl-2-oxocyclohexanepropionic acid methyl ester, bp 117° - 120° C/0.4mm, and 1-propyl-2-oxocyclohexanepropionic methyl ester, νmaxCHCl3 1735, 1700cm-1, are obtained, respectively. νmaxCHCl3 1735, 1700cm-1, are obtained