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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 23
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Original Articles

Oxidation of Benzyl Halides to Aldehydes and Ketones with Potassium Nitrate Catalyzed by Phase-Transfer Catalyst in Aqueous Media

, , , &
Pages 4188-4197 | Received 20 Feb 2008, Published online: 31 Oct 2008
 

Abstract

The catalytic oxidation of benzyl halides to aldehydes and ketones in aqueous media was studied under relatively mild reaction conditions by using phase-transfer catalyst combined with potassium nitrate and 10% aqueous potassium hydroxide solution. As a result, a simple high-yield procedure has been developed.

Notes

a Reaction conditions: 4-isopropylbenzyl chloride (0.1 mol), H2O (15 mL), reflux.

b Isolated yield.

c About 2 g cumenic acid (mp: 117–119 °C, lit.[22] mp 118–120 °C) was obtained by acidifying the reaction aqueous solution with hydrochloric acid.

d Added 10% KOH aqueous solution (60 mL, 0.1 mol) dropwise over the indicated time with a dropping funnel.

a Reaction conditions: 4-isopropylbenzyl chloride (0.1 mol), KNO3 (0.11 mol), H2O (15 mL), PTC (1.1 mmol); 10% KOH aqueous solution (60 mL, 0.11 mol) added dropwise with a dropping funnel over 4 h, reflux.

b Isolated yield.

a Reaction conditions: benzyl halide (0.1 mol), KNO3 (0.11 mol), H2O (15 mL), CTAB (1.1 mmol), 10% KOH aqueous solution (60 mL, 0.11 mol) added dropwise with a dropping funnel over the indicated time, reflux.

b Isolated yield.

c An intractable mixture.

d 2-Bromoethylbenzene was used.

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