Benzoic Acid → Triphenylsulfonium 2-benzoyloxyethanesulfonate

Beteiligte Stoffe

Reaktionsschritte

In 25 g of trifluoroacetic acid were dissolved 3.0 g (20 mmol) of sodium isethionate and 2.4 g (20 mmol) of benzoic acid. To this solution, 6.3 g (30 mmol) of trifluoroacetic anhydride was added dropwise, followed by stirring for 2 hours at room temperature. Then 90 g (30 mmol) of an aqueous solution of triphenylsulfonium chloride prepared in Synthesis Example 1-1 and 120 g of methylene chloride were added, followed by stirring for 30 minutes at room temperature. At the end of stirring, the organic layer was taken out, aqueous sodium bicarbonate was added dropwise until the pH of the aqueous layer ceased to be acidic, and the organic layer was then taken out. The organic layer was washed with water and concentrated in vacuum. Methyl isobutyl ketone was added to the concentrate, which was concentrated in vacuum again while distilling off the residual water. Diisopropyl ether was added to the residue. Subsequent decantation and drying gave the target compound, triphenylsulfonium 2-benzoyloxyethanesulfonate. Colorless oily matter, 3.0 g, yield 30%. The compound, designated PAG-3, has the following structure.

Herkunft & Nachweise