Albright-Goldman oxidation

What is Albright-Goldman oxidation?

The initial report of this process was provided by Albright and Goldman of the American Cyanamid Company in 1965.

Albright-Goldman oxidation involves a gentle transformation of primary and secondary alcohols into corresponding aldehydes and ketones using a blend of dimethyl sulfoxide (DMSO) and acetic anhydride as an oxidizing agent. This procedure is especially beneficial for converting sterically hindered hydroxyl groups.

Albright-Goldman oxidation
Albright-Goldman oxidation

R’ = H, alkyl or aryl

Typically, the oxidation reaction is performed by allowing a mixture containing 1 millimole of primary or secondary alcohol, 3 mL of DMSO, and 2 mL of acetic anhydride (an excess of 20 mmol) to stand at room temperature for 18 to 24 hours.

The conversion of primary and secondary alcohols into corresponding aldehydes and ketones using this reaction has been widely employed, especially for alcohols with steric hindrance.

This process has found frequent application in carbohydrate modification. However, when attempting to oxidize phenols with DMSO/Ac2O, the reaction results in the thiomethoxymethylation of the corresponding phenols.

References

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