Dess-Martin Periodinane

Used Chemicals

• trans-2-Phenyl-1-cyclohexanol [P1174]
• Dess-Martin Periodinane (= DMP) [D2045]
• Dichloromethane

Procedure

To dichloromethane (10 mL) was added trans-2-phenyl-1-cyclohexanol (0.30 g，1.7 mmol) and DMP (0.72 g, 1.7 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature, then diluted with diethyl ether and washed with saturated aqueous sodium bicarbonate, 10% aqueous sodium thiosulfate, water and brine. The organic layer was concentrated under reduced pressure. The resulting crude product was purified by column chromatography (hexane:ethyl acetate = 8:1 on silica gel) to give 1 as a white solid (0.22 g, 74% yield).

Experimenter’s Comments

The reaction mixtures were monitored by TLC (hexane:ethyl acetate = 4:1).

Analytical Data（2-Phenylcyclohexanone (1)）

¹H NMR (400 MHz, CDCl₃); δ 7.37-7.31 (m, 2H), 7.30-7.22 (m, 1H), 7.17-7.12 (m, 2H), 3.62 (dd, 1H, J = 12.4, 6.9 Hz), 2.58-2.41 (m, 2H), 2.33-2.23 (m, 1H), 2.22-2.10 (m, 1H), 2.10-1.94 (m, 2H), 1.91-1.75 (m, 2H).

¹³C NMR (101 MHz, CDCl₃); δ 210.5, 138.9, 128.6, 128.5, 127.0, 57.5, 42.3, 35.2, 27.9, 25.5.

Lead Reference

• Acceleration of the Dess-Martin Oxidation by Water
• S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549.

References

• M. Horikawa, K. Hashimoto, H. Shirahama, Tetrahedron Lett. 1993, 34, 331.
• J. N. Haseltine, M. P. Cabal, N. B. Mantlo, N. Iwasawa, D. S. Yamashita, R. S. Coleman, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1991, 113, 3850.
• J. P. Burkhart, N. P. Peet, P. Bey, Tetrahedron Lett. 1988, 29, 3433.
• D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.
• R. J. Linderman, D. M. Graves, Tetrahedron Lett. 1987, 28, 4259.