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

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.

peroxodisulfate - alcohols - hydroquinones - oxidation

References and Notes

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<A NAME="RD05506ST-9">9</A>

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]

<A NAME="RD05506ST-10">10</A>

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.

<A NAME="RD05506ST-11">11</A>

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.

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