M-Xylene → 1-(3-Methylbenzyl)oxy-4-acetamido-2,2,6,6-tetramethylpiperidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.67 g (0.05 mol) of 1-oxyl-4-acetamido-2,2,6,6-tetramethylpiperidine and 106.17 g (1.0 mol) of m-xylene under a nitrogen atmosphere is heated at 133° C. for 67 hours. The reaction mixture is filtered to remove the hydroxylamine, and the filtrate is washed with 10 w/v % ascorbic acid (3×33 mL) and distilled water (2×50 mL). The organic phase is dried over anhydrous sodium sulfate and the volatiles are removed in vacuo. The residue is recrystallized from acetonitrile to give 4.03 g (51% yield) of a white solid melting at 163-164.5° C.

Provenance & Evidence