p-Toluenesulfonic acid → Sodium 2-cyclohexanecarbonyloxyethanesulfonate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 3.0 g (20 mmol) of sodium isethionate, 7.7 g (60 mmol) of cyclohexanecarboxylic acid, and 0.38 g (2 mmol) of tosylic acid was heated at 200° C. for 20 hours. Diethyl ether was added to the reaction solution, yielding 4.7 g of sodium 2-cyclohexanecarbonyloxyethanesulfonate. A 1.4-g portion of the sodium salt was combined with 23 g (10 mmol) of an aqueous solution of triphenylsulfonium chloride prepared in Synthesis Example 1-1 and 30 g of methylene chloride, followed by stirring for 12 hours at room temperature. At the end of stirring, the organic layer was taken out, 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. Diethyl ether was added to the residue, followed by decantation and purification by column chromatography. There was obtained the target compound, triphenylsulfonium 2-cyclohexanecarbonyloxyethanesulfonate. Colorless oily matter, 1.7 g, yield 66% as calculated from the sodium salt. The compound, designated PAG-4, has the following structure.

Herkunft & Nachweise