Acetic Acid → HCID 22463279, compound

Participants

Reaction Steps

A solution of 0.116 g (0.429 mmol) of ferric chloride hexahydrate and 0.096 g (1.60 mmol) of glacial acetic acid in 2 ml of water is added to a mixture of 5.08 g (11.6 mmol) of 1-oxyl-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, 40 ml of cyclohexane, and 60 ml of acetonitrile that has been heated to 60°. A solution of 3.36 g (49.4 mmol) of aqueous 50% hydrogen peroxide is added to the reaction mixture dropwise over 2.5 hours at the reflux temperature of 60-62°. A solution of 0.033 g of ferric chloride hexahydrate and 0.040 g of glacial acetic acid in 1 ml of water is added to the reaction mixture 1.5 hours after the peroxide addition is begun. A solution of 0.031 g of ferric chloride and 0.028 g of glacial acetic acid in 1 ml of water is added to the reaction mixture 4 hours after the peroxide addition is begun. After being heated a total of 5 hours at reflux temperature, the reaction mixture is cooled and excess peroxide is decomposed by the addition of aqueous sodium sulfite solution. The organic layer is concentrated and purified by flash chromatography with 20:1 heptane-ethyl acetate to afford 4.27 g (71% yield) of the title compound, a white solid, mp 42-46. The assay is approximately 90% by NMR integration.

Provenance & Evidence