4-Toluenesulfonyl chloride → HCID 19773482, compound

Participants

Reaction Steps

To a stirred solution of 0.5 mol of 4-[N-2-hydroxyethyl-N-methylamino]benzaldehyde in methylene chloride at 0° C. are added 0.51 mol of p-toluenesulfonyl chloride, 0.51 mol of triethylamine, and 0.005 mol of N,N-dimethylaminopyridine, and the reaction medium is warmed slowly to room temperature. After standing at room temperature for one hour, the reaction product medium is washed with cold 1N HCL, saturated sodium bicarbonate solution, and water. The organic solution is separated and dried over molecular sieves, filtered through cotton, and evaporated to yield the 4-[N-2-tosylethyl-N-methylamino]-benzaldehyde as a crystalline product, which then is recrystallized from ethanol.

Provenance & Evidence