Potassium Iodide → (4-Hydroxy-3,5-dimethylphenyl)(diphenyl)sulfanium iodide

Participants

Reaction Steps

To a mixture of 36 g of 2,6-xylenol and 60 g of diphenyl sulfoxide was added 300 mL of a solution consisting of diphosphorous pentoxide/methanesulfonic acid=1/10. The resultant reaction mixture was reacted at 40° C. for 4 hours and then poured on ice. This aqueous solution was washed with ethyl acetate. To the aqueous phase was added a solution prepared by dissolving 200 g of potassium iodide in water. The particles precipitated were taken out by filtration and washed with acetone. As a result, 3,5-dimethyl-4-hydroxyphenyldiphenylsulfonium iodide was obtained in an amount of 80 g. To 7.1 g of the 3,5-dimethyl-4-hydroxyphenyldiphenylsulfonium iodide obtained were added 300 mL of chloroform and 2.0 g of triethylamine. To this solution was dropwise added 10 g of nonafluorobutanesulfonic anhydride over 30 minutes with cooling with ice. After the resultant reaction mixture was reacted at room temperature for 1 hour, water was added thereto. The organic phase was washed with 5% aqueous NaOH solution and subsequently with water and then concentrated to obtain a crude reaction product, which was recrystallized from ethyl acetate/dilsopropyl ether. As a result, acid generator (Bb-1) was obtained in an amount of 10.0 g.

Provenance & Evidence