4-N-propan-2-ylbenzene-1,4-diamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following essentially the procedure of Example 1, 66.0 g (0.25 mole) N-isopropyl-4-nitrosoaniline, 20 g (50%) sodium hydroxide and 264 g n-hexanol were kept at 100° C. for 1.5 hours. HPLC analysis of the reaction mixture indicated absence of the nitroso starting compound. By vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product were recovered (48.6 wt. % yield). By vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product were recovered (48.6 wt. % yield)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following essentially the procedure of Example 1, 66.0 g (0.25 mole) N-isopropyl-4-nitrosoaniline, 20 g (50%) sodium hydroxide and 264 g n-hexanol were kept at 100° C. for 1.5 hours. HPLC analysis of the reaction mixture indicated absence of the nitroso starting compound. By vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product were recovered (48.6 wt. % yield). By vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product were recovered (48.6 wt. % yield)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromomethyl-2,6-di-tert-butyl-phenol (2.42 g, 0.008 mole) was dissolved in 50 mL of dry tetrahydrofuran. In a separate conical flask N-Isopropyl-benzene-1,4-diamine (2.40 g, 0.016 mole) was dissolved in 25 mL of tetrahydrofuran and solution was transferred to a cylindrical funnel with pressure equalizing tube. Three-necked round-bottomed flask containing solution of 4-Bromomethyl-2,6di-tert-butyl-phenol was kept in oil-bath at 85° C. Solution in the flask was continuously stirred with the help of magnetic stirrer. N-Isopropyl-benzene-1,4-diamine solution was added drop-by-drop, from funnel to the flask in acidic medium for a span of 4-5 hours till all the solution was poured out. The reaction was terminated after that and the final reaction mixture was allowed to attain room temperature. The product was purified using silica gel column chromatography. Product was identified by 1H-NMR. The yield of 2,6di-tert-butyl4-[(4isopropylamino-phenylamino)methyl]-phenol is 2.025 g (68%). solution was transferred to a cylindrical funnel with pressure was kept in oil-bath at 85° C was poured out The reaction was terminated after that and the final reaction mixture to attain room temperature The product was purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following essentially the procedure of Example 1, 66.0 g (0.25 mole) N-isopropyl-4-nitrosoaniline, 20 g (50%) sodium hydroxide and 264 g n-hexanol were kept at 100° C. for 1.5 hours. HPLC analysis of the reaction mixture indicated absence of the nitroso starting compound. By vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product were recovered (48.6 wt. % yield). By vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product were recovered (48.6 wt. % yield)