Oxidative cleavage of an alkene with catalytic ruthenium tetroxide; 2-acylphenylacetic acid

Meriel Kimberley ([email protected]),
A contribution from the Booker-Milburn Group, Bristol

Chemicals Used
3-methyl-indene, sodium periodate (Aldrich), ruthenium trichloride hydrate (Aldrich), acetonitrile (HPLC grade, Aldrich), hexane water

Procedure
To a solution of 3-methyl-indene (497 mg, 3.8 mmol) in acetonitrile (7 ml), hexane (7 ml) and water (10 ml) was added sodium periodate (3.35 g, 15.7 mmol) followed by ruthenium trichloride (17 mg, 0.08 mmol, 2.2 mol%). The entire mixture was then stirred at room temperature for 2 hours until the reaction was complete (TLC). Dichloromethane was then added (30 ml), the phases separated and the upper phase was extracted with dichloromethane (3 x 30 ml). The combined organic extracts were dried (MgSO₄) and concentrated in vacuo. Diethyl ether was added to the resulting residue (to precipitate any remaining inorganic species). The resulting solution was filtered through a pad of celite and concentrated to afford the crude keto-acid which could be used without further purification. Pure compound can be obtained by recrystallisation from ethyl acetate.

Author's Comments
Care should be taken to ensure vigorous stirring after addition of ruthenium trichloride as the reaction solution can get very warm.

Data
¹H (CDCl₃): 7.84 (1H, d, J 7.7 Hz, CH), 7.51 (1H, t, J 7.7 Hz, CH), 7.42 (1H, t, J 8 Hz), 7.35 (1H, d, J 8 Hz, CH), 3.91 (2H, s, CH₂) and 2.65 (3H, s, CH₃).

Lead Reference
P. H. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J.Org. Chem., 1981, 46, 19, 3936-3938.

Other References
M. Shindo, Y. Sato, K. Shishido, J. Org. Chem., 2001, 66, 23, 7818-7824.

This page has been viewed approximately 239 times since records began.

Get CDX file (Choose "Open this file from its current location" TWICE)

SyntheticPages^TM are for use exclusively by those with training and experience in synthetic chemistry. While contributors are asked to identify hazards and to use methods designed to reduce risk, no formal hazard or risk assessments are included, and these procedures must be conducted at one's own risk. SyntheticPages, its editors, owners and associates do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. Copyright ©2002 Synthetic Pages

Comment on this page!