Phenol → 2,6-Bis(1-methylethyl)-4-phenoxybenzenamine

Participants

Reaction Steps

With stirring, 21 g (0.15 mol) of potassium carbonate are initially added to 141 g (1.5 mol) of phenol in 500 g of toluene, followed by the addition of 168 g (1.5 mol) of a 50% aqueous solution of potassium hydroxide. The entire water of reaction is then separated under reflux, and then ca. 400 g of toluene are removed by distillation. The residue is dissolved in 700 g of dimethyl formamide. After addition of 6 g (0.05 mol) of copper carbonate, solvent is distilled off until the temperature of the reaction mixture is 140° C. Then 256 g (1 mol) of 4-bromo-2,6-diisopropylaniline are added at 140° C. and the mixture is kept for 10 hours at 140° C. The dimethyl formamide is then removed by vacuum distillation, the residue is extracted with water, and the product is taken up in toluene. After stripping off the toluene, the crude product is purified by vacuum distillation, giving 215 g (80% of theory) of 4-phenoxy-2,6-diisopropylaniline with a boiling point of 142°-145° C./0.04 mbar and a melting point of 69°-71° C., in the form of a bright red product. Conversion to the hydrochloride is effected by dissolving the product in 300 g of butyl acetate, adding 115 g of a 37% solution of hydrochloric acid, and removing the water of reaction by vacuum distillation. The hydrochloride is isolated by filtration, washed with butyl acetate and dried under vacuum, giving 235 g (96% of theory, based on 4-phenoxy-2,6-diisopropylaniline) of 4-phenoxy-2,6-diisopropylaniline hydrochloride in the form of white crystals which melt at 247°-249° C.

Provenance & Evidence