Potassium Carbonate → N-(2',6'-dichloro-4'-methylphenyl)-4-methylaniline

Participants

Reaction Conditions

Reaction Steps

12 g (67 mmol) of 2,6-dichloro-4-methylphenol are dissolved in 25 ml of 2-propanol followed by the addition of 10.5 g (76 mmol) of potassium carbonate and 12.8 g (70 mmol) of 2-chloro-N-(4-methylphenyl)acetamide. The mixture is refluxed for 4 h. At this time, the formation of A: 2-(2′,6′-dichloro-4′-methylphenoxy)-N-(4-methylphenyl)acetamide is completed. 13.6 ml of sodium methylate solution 30% in methanol are slowly added and the temperature is increased to about 85° C. by distilling 25 ml of solvent. The mixture is stirred 2 h more to complete the formation of B. 25 ml of water are added at 70° C. to obtain a 2 phases solution. The lower layer is discarded. The upper layer is diluted with 20 ml of heptane-fraction and washed with 2×20 ml of water. The organic phase is separated and concentrated in vacuo to obtain N-(2′,6′-dichloro-4′-methylphenyl)-4-methylaniline as a crude oil. GC/MS: 265 (100, M+), 195 (130).

Provenance & Evidence