P-Anisidine → HCID 135727396, compound

Participants

Reaction Steps

To a mixture of 35 g (0.085 mole) 3-octadecyloxy-2-naphthol, 12 g (0.30 mole) sodium hydroxide, 500 ml methanol, and 1000 ml tetrahydrofuran at 0°-5° was added a diazonium salt solution prepared from 10.5 g (0.085 mole) p-anisidine in 40 ml water containing 20 ml concentrated hydrochloric acid and a solution of 5.9 g (0.005 mole) sodium nitrite in 40 ml water. The mixture was stirred at 0°-5° for 1 hour and at room temperature for 1 hour then acidified with 40 ml acetic acid in 1000 ml water. There was obtained 40.5 g of a red solid, which was recrystallized from ethyl acetate to give red crystals, m.p. 95°-97° C.

Provenance & Evidence