Experiment 15: Aerobic Oxidation of an Alcohol Using a Cu/TEMPO Catalyst System

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Cu/TEMPO oxidation

Chemical Safety Information:

Reagents, Products, and Solvents
m-nitrobenzyl alcohol p-nitrobenzyl alcohol piperonyl alcohol
4-isopropylbenzyl alcohol 4-chlorobenzyl alcohol 4-bromobenzyl alcohol
4-methoxybenzyl alcohol 4-methylbenzyl alcohol cuprous bromide
N-methylimidazole TEMPO 2,2′-bipyridyl
magnesium sulfate deuterated chloroform  

 

Recommended Reading:

Hoover, J. M.; Stahl, S. S. Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols. J. Am. Chem. Soc., 2011, 133 (42), 16901–16910.

Ryland, B. L.; Stahl, S. S. Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems. Angew. Chem. Int. Ed. 2014, 53, 8824-8838.

 

 

Sample 1H-NMR Spectra for All Products (not available for submission for credit)

 

Stock FID 1H-NMR 3-nitrobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock FID 1H-NMR 4-nitrobenzaldehyde (available for submission for credit)

Stock FID 1H-NMR piperonal (available for submission for credit)

Stock FID 1H-NMR 4-isopropylbenzaldehyde (available for submission for credit)

Stock FID 1H-NMR 4-chlorobenzaldehyde (available for submission for credit)

Stock FID 1H-NMR 4-bromobenzaldehyde (available for submission for credit)

Stock FID 1H-NMR 4-methoxybenzaldehyde (available for submission for credit)

Stock FID 1H-NMR 4-methylbenzaldehyde (available for submission for credit)

 

 

Stock IR 3-nitrobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock IR 4-nitrobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock IR piperonal (available for submission for credit, see laboratory manual for details)

Stock IR 4-isopropylbenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock IR 4-chlorobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock IR 4-bromobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock IR 4-methoxybenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock IR 4-methylbenzaldehyde (available for submission for credit, see laboratory manual for details)

 

Stock GC-MS 3-nitrobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock GC-MS 4-nitrobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock GC-MS piperonal (available for submission for credit, see laboratory manual for details)

Stock GC-MS 4-isopropylbenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock GC-MS 4-chlorobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock GC-MS 4-bromobenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock GC-MS 4-methoxybenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock GC-MS 4-methylbenzaldehyde (available for submission for credit, see laboratory manual for details)