1H NMR – 60 MHz Permanent Magnet System – Reaction Monitoring

Below are a few further examples of acetylation reactions of acetic anhydride with an excess of alcohol. The alcohols include tert-butanol and isopropanol.

Reaction 1: Acetylation of t-butyl alcohol with acetic anhydride in the presence of acid.

Acetylation of t-butanol with acetic anhydride - 1H NMR Reaction Monitoring

Reaction 2: Acetylation of Isopropanol with acetic anhydride in the presence of acid.

Acetylation of isopropanol with acetic anhydride - 1H NMR Reaction Monitoring

Reaction 3: Methoxyacetone and hydroxylamine reaction in methanol to form an Oxime

Oxime Production from Ketone and Hydroxylamine - 1H NMR Reaction Monitoring

Oxime Production from Ketone and Hydroxylamine - Zoomed spectrum - 1H NMR Reaction Monitoring

Resolution of the methylenes in the methoxyacetone and the reaction product is readily observed.

Oxime from ketone and hydroxylamine - assignment - 1H NMR Reaction Monitoring

All the above experiments were performed in an NMR tube. We are currently looking at the same reactions under flow conditions utilizing a HPLC pump and PEEK tubing to transport sample to the NMR probe at 5 ml/min.