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Synlett 2006(11): 1724-1728  
DOI: 10.1055/s-2006-944195
LETTER
© Georg Thieme Verlag Stuttgart · New York

{-N+(CH3)2CH2CH2N+[(CH3)2](CH2)4-}n S2O8 2-: A Selective and Recyclable ­Reagent for Oxidation of Alcohols and Hydroquinones in Water

Mahmood Tajbakhsh*, Moslem Mansour Lakouraj*, Farhad Ramzanian-Lehmali
Department of Chemistry, Mazandaran University, Babolsar, Iran
Fax: +98(11)25242002; e-Mail: Tajbaksh@umz.ac.ir;
Further Information

Publication History

Received 19 February 2006
Publication Date:
04 July 2006 (online)

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Abstract

This article describes the oxidation of alcohols and ­hydroquinones in water using polymer-supported peroxodisulfate, which has been prepared by mixing an aqueous solution of 2,4-ionene with an aqueous solution of potassium peroxodisulfate at room temperature.

Key words

peroxodisulfate - alcohols - hydroquinones - oxidation

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Preparation of {-N + (CH 3 ) 2 CH 2 CH 2 N + [(CH 3 ) 2 ](CH 2 ) 4 -} n S 2 O 8 ²- (P-S 2 O 8 ). To an aqueous solution of polymer (1 g, 5 mL of H2O) was added a solution of K2S2O8 (1.62 g, 6 mmol in 30 mL of H2O). The mixture was stirred at r.t. for 30 min. The resulting white solid was filtered, washed with distilled H2O (10 mL) and dried over CaCl2 in a desiccator under vacuum. The content of active oxidizing agent (S2O8 2-) was determined by titration. [8]

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Typical Procedure for Oxidation of Alcohols and Hydroquinone with P-S 2 O 8 .
A mixture of alcohol or hydroquinone (1 mmol), H2O (10 mL) and P-S2O8 (0.36 g, ca. 1 mmol) was placed in a 25-mL round-bottom flask and was stirred and heated to reflux. After completion of the reaction (monitored by TLC), the reaction mixture was cooled, and extracted with Et2O (3 × 10 mL). The combined organic layers were washed with brine, dried over anhyd Na2SO4, and solvent evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to afford pure material.

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Typical Procedure for Recycled P-S 2 O 8 .
The solvated polymer in aqueous phase after completion of the reaction was washed with Et2O and recycled with added solution of K2S2O8 (in H2O). The resulting white solid product was filtered, washed with Et2Ο (3 × 10 mL) and cooled distilled H2O (10 mL) and dried over CaCl2 in a desiccator under vacuum for subsequent reaction.