Sodium Hydroxide → HCID 21097647, compound

Participants

Reaction Steps

267 g of 4-fluorophenyldiphenylsulfonium trifluoromethanesulfonate was dissolved in 2,000 g of dichloromethane, and the atmosphere of the system was replaced with nitrogen. After the addition of 2,000 g of a 10 wt % sodium hydroxide aqueous solution, 58 g of tetra-n-butylammonium bromide, and 72.1 g of cyclohexanethiol to the solution, the mixture was stirred at room temperature for 30 minutes. The mixture was transferred to a separating funnel, and allowed to stand. The aqueous layer was then removed. After washing the organic layer with 3,000 ml of distilled water, the aqueous layer was removed. The resulting dichloromethane solution was dried over anhydrous magnesium sulfate, and filtered. After evaporating dichloromethane from the solution, the residual liquid was dried under reduced pressure to obtain 192 g of 4-cyclohexylthiophenyldiphenylsulfonium trifluoromethanesulfonate. 192 g of 4-cyclohexylthiophenyldiphenylsulfonium trifluoromethanesulfonate was dissolved in 3,000 ml of methanol in a reaction flask. After the addition of 180 g of a 30 wt % hydrogen peroxide solution and 105 g of sodium tungstate dihydrate to the solution, the mixture was stirred at room temperature for 30 minutes. The resulting methanol solution was concentrated under reduced pressure, and the residue was dissolved in 3,000 g of dichloromethane. The solution was transferred to a separating funnel, and allowed to stand. The aqueous layer was then removed. After washing the organic layer with 1,000 ml of distilled water, the aqueous layer was removed. The resulting dichloromethane solution was dried over anhydrous magnesium sulfate, and filtered. After evaporating dichloromethane from the solution, the residual liquid was dried under reduced pressure to obtain 145 g of 4-cyclohexylsulfonylphenyldiphenylsulfonium trifluoromethanesulfonate. 145 g of 4-cyclohexylsulfonylphenyldiphenylsulfonium trifluoromethanesulfonate was dissolved in 1,000 g of methanol. The solution was subjected to ion-exchange chromatography (ion-exchange resin: Sephadex QAE A-25 manufactured by Aldrich (600 g)), and the collected organic layer was evaporated under reduced pressure to obtain 89 g of the compound represented by the following formula (XX).

Provenance & Evidence