Triethylamine → Bis(4-tert-butoxyphenyl)(4-dimethylaminophenyl)sul fonium p-toluenesulfonate

Participants

Reaction Steps

A solution of 8.5 grams (0.025 mol) of bis(4-tert-butoxyphenyl) sulfoxide in 300 grams of methylene chloride was cooled in an ice water bath. To the solution, 1.3 grams (0.013 mol) of triethylamine was added and 12.2 grams (0.05 mol) of trimethylsilyl-p-toluenesulfonate was added dropwise in a controlled manner so that the temperature might not exceed 10° C. The reaction solution was ripened for 30 minutes while maintaining a reaction temperature of 0° to 10° C. A Grignard reagent, which was separately prepared in a conventional manner using 10.0 grams (0.05 mol) of 4-bromo-N,N-dimethylaniline, 1.2 grams (0.05 mol) of magnesium and 50 grams of THF, was added dropwise to the reaction solution in a controlled manner so that the temperature might not exceed 10° C. The reaction solution was ripened for 30 minutes while maintaining a reaction temperature of 0° to 10° C. 200 grams of an aqueous solution of 20% ammonium chloride was added to the reaction solution to terminate reaction. After separation, 200 grams of chloroform was added to the organic layer. After the organic layer was washed twice with 200 grams of water, the solvent was distilled off in vacuum, yielding an oily residue. The oily residue was recrystallized, isolating 7.6 grams (yield 49%) of bis(4-tert-butoxyphenyl)(4-dimethylaminophenyl)sul fonium p-toluenesulfonate with 99% purity.

Provenance & Evidence