Oxidation of Primary Alcohols To Carboxylic Acids - PDC in DMF (Corey and Schmidt)

PDC in DMF (Corey and Schmidt)

Pyridinium dichromate (PDC) is a bright-orange solid with the formulae (C₅H₅NH)₂Cr₂O₇ that is very often used for the oxidation of primary and secondary alcohols to aldehydes and ketones respectively. On the other hand, in 1979, Corey and Schmidt reported that reaction of saturated primary alcohols with PDC, using dimethylformamide (Me₂NCHO, DMF) as solvent, results in oxidation to carboxylic acids rather than aldehydes. Interestingly, no oxidation to carboxylic acids occurs on allylic and benzylic primary alcohols. The procedure of Corey and Schmidt for the oxidation of saturated primary alcohols to carboxylic acids is run under essentially neutral conditions.