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Synlett 2007(10): 1565-1568  
DOI: 10.1055/s-2007-982550
LETTER
© Georg Thieme Verlag Stuttgart · New York

In Situ Generation of 2-Iodoxybenzoic Acid (IBX) in the Presence of Tetraphenylphosphonium Monoperoxysulfate (TPPP) for the Conversion of Primary Alcohols into the Corresponding Aldehydes

Philip C. Bulman Page*a, Louise F. Applebya, Benjamin R. Buckleya, Steven M. Allina, Michael J. McKenzieb
a Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK
Fax: +44(1509)223926; e-Mail: p.c.b.page@lboro.ac.uk;
b Charnwood Molecular Ltd., The Heritage Building, Beaumont Court, Prince William Road, Loughborough, Leicestershire LE11 5GA, UK
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Publikationsverlauf

Received 11 April 2007
Publikationsdatum:
06. Juni 2007 (online)

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Abstract

Primary alcohols are oxidized to the corresponding aldehydes by tetraphenylphosphonium monoperoxysulfate (TPPP) in the presence of catalytic 2-iodobenzoic acid. Overoxidation to ­carboxylic acids is not observed, in contrast to the use of catalytic 2-iodobenzoic acid with Oxone® as reoxidant.

Key words

IBX - TPPP - Oxone® - oxidation - aldehyde - alcohol

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13

Conversions based on 1H NMR data.

14

The typical active oxygen content of TPPP is about 80%.

16

The alcohols in Tables [3] and [4] are commercially available and were used as received.

17

Representative Experimental Procedure
Piperonyl alcohol (0.06 g, 5 mmol) was dissolved in DCE (5 mL) and 2-iodobenzoic acid (0.02 g, 0.1 mol%) was added. The reaction was heated with stirring to 80 °C, and the reaction progress monitored by TLC. Once the alcohol had been consumed, the reaction mixture was allowed to cool to r.t., and Et2O (10 mL) was added. The excess TPPP was removed by passage through Celite®, and the solvent removed to give piperonal as a colorless solid (0.05 g, 90%), >95% pure by 1H NMR spectroscopy.