Thionyl Chloride → HCID 21458935, compound

Participants

Reaction Steps

A Grignard reagent was conventionally prepared using 51.3 g (0.2 mol) of 3,4-di-tert-butoxyphenyl chloride, 4.9 g (0.2 mol) of magnesium, and 100 g of THF. The Grignard reagent solution was cooled in an ice water bath whereupon 5.8 g (0.049 mol) of thionyl chloride diluted with 10 g of THF was added dropwise at less 30° C. Reaction mixture was ripened for about 30 minutes. Thereafter, 26.7 g (0.12 mol) of trimethylsilyltrifluoromethane sulfonate was added dropwise at less 20° C. Reaction mixture was further ripened for 1 hour and thereafter, the reaction solution was allowed to stand overnight at room temperature. After the reaction solution was again cooled in an ice water bath, 200 g of 16.7% ammonium chloride aqueous solution was added thereto at less 30° C. After separation, 100 g of chloroform was added to the organic layer, which was washed three times using 100 g of water. Thereafter, the solvent was distilled off under reduced pressure by means of a rotary evaporator, obtaining an oily residue. The oily residue was recrystallized, isolating tris(3,4-di-tert-butoxyphenyl)sulfonium trifluoromethanesulfonate of 99% purity in an amount of 13.2 g (yield 32%).

Provenance & Evidence