Methanol → 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

Participants

Reaction Conditions

Reaction Steps

The above-obtained 1-(4-nitrophenyl)-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]diazene (6.0 g) and sodium dithionite (14.6 g) were added to a mixture of methanol (30 mL) and water (30 mL), and the mixture was stirred at 65 to 70° C. for 2 hours under a nitrogen atmosphere. The mixture was cooled to room temperature, and further stirred at 0 to 5° C. for one hour. Precipitated crystals were collected by filtration, and washed with a mixture of methanol and water again to obtained wetted crystals. The wetted crystals were added to a mixture of toluene and 2N aqueous sodium hydroxide. An organic layer was separated and concentrated. The concentrate was recrystallized from a mixture of water and methanol, and the resultant crystals were dried under reduced pressure to obtain the title compound (3.5 g., yield 86%).

Provenance & Evidence