Peracetic Acid → 3-((R)-5-Cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane

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Reaction Conditions

Reaction Steps

A flask was charged with 11.48 g (51.6 mmol) of crude (3R)-(3,7-dimethyl-oct-6-enyl)-cyclohexane, 100 mL of dichloromethane, and 9.33 g (111 mmol) of sodium bicarbonate. The mixture was cooled in a 0° C. bath. Slowly 11.6 mL (55.2 mmol) 32% peracetic acid was added. The mixture was stirred for 4 hours at 0° C. Then 10% aqueous sodium sulfite was added slowly until bubbling ceased. The layers were separated, and the organic layer was washed twice with 10% aqueous sodium sulfite and dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The remaining residue was 10.65 g (87%) of a clear oil: 1H NMR (400 MHz, CDCl3) ppm 0.86 (m, 5H) 1.00 (d, J=6.59 Hz, 2H) 1.14 (m, 7H) 1.25 (s, 3H) 1.29 (s, 3H) 1.35 (m, 2H) 1.50 (m, 3H) 1.65 (m, 5H) 2.68 (td, J=6.16, 1.83 Hz, 1H). MS (APCI) m+1/z=239.

Provenance & Evidence