Réaction #1929019

Équation de réaction

1,4,7-Tris(p-toluenesulfonyl)-1,4,7-triazacyclononane

phenol

→

1-(p-toluenesulfonyl)-1,4,7-triazacyclononane

Rendement 88.0%

Solvants

HBr

acetic acid

—

solution

Conditions de réaction

Traitement

1. 1
   AutreAfter returning to ambient temperature
2. 2
   Filtrationthe mixture is filtered
3. 3
   Lavagethe solid is washed with diethyl ether (2×80 ml)
4. 4
   workup.DISSOLUTIONThe hydrobromide salt is dissolved in a 1M sodium hydroxide solution until the pH
5. 5
   ExtractionThe aqueous solution is extracted with chloroform (8×50 ml)
6. 6
   SéchageThe combined organic phases are dried over Na2SO4
7. 7
   Autrethe solvent is evaporated under vacuum
8. 8
   AutreFinally, a white solid is obtained (7.36 g, yield 88%)

Mode opératoire

1,4,7-Tris(p-toluenesulfonyl)-1,4,7-triazacyclononane (17.56 g, 29.7 mmol) and phenol (21 g, 223.0 mmol) are dissolved in 240 ml of a solution of HBr (33%) in glacial acetic acid. The solution is heated at 90° C. for 30 h. A solid appears after 3 h. After returning to ambient temperature, the mixture is filtered and the solid is washed with diethyl ether (2×80 ml). The hydrobromide salt is dissolved in a 1M sodium hydroxide solution until the pH is of the order of 12 units. The aqueous solution is extracted with chloroform (8×50 ml). The combined organic phases are dried over Na2SO4 and the solvent is evaporated under vacuum. Finally, a white solid is obtained (7.36 g, yield 88%).

Source