P-Anisidine → HCID 136409737, compound

Participants

Reaction Conditions

Reaction Steps

To 20 g (0.042 mole) of 3-hydroxy-2-[4-(2,4-di-t-pentylphenoxy)-n-butyl]naphthamide in 200 ml tetrahydrofuran was added a solution of 8 g sodium hydroxide in 200 ml methanol. The mixture was cooled to 0° C. and treated with a diazonium solution prepared from a solution of 5.2 g (0.042 mole) p-anisidine in 40 ml water containing 10 ml conc. hydrochloric acid and a solution of 2.9 g (0.042 mole) sodium nitrite in 30 ml water. Then 400 ml water was added, and the mixture was stirred at 0° C. for 2 hrs. and at room temperature for one hour. The oil which separated after acidification with 30 ml acetic acid was extracted with ether. The solution was dried and concentrated to 21 g of a red oil which was used without further purification in the next step.

Provenance & Evidence