1-Naphthol → HCID 19959520, compound

Participants

Reaction Steps

2-Naphthol (14.43 g; 0.100 mol) was dissolved in toluene (200 ml) by warming. The pale brown solution was cooled and vigorously stirred until the naphthol began to precipitate and chlorine (15.22 g;0.21 mol) was then passed through the solution at approximately 2.5-3.0 g/min followed immediately by nitrogen gas. The resulting amber solution was treated firstly with triethylamine (12.12 g;0.12 mol) in one portion and then with a solution of pyrrolidine (7.10;0.10 mol), in toluene (100 ml), dropwise over 1.5 hours keeping the temperature at 15°-20° C. The resulting brown mixture was filtered to remove triethylamine hydrochloride as a white amorphous solid. The toluene filtrate was washed with water, dried and evaporated to give 1-chloro-4-pyrrolidino-2-naphthol as a brown viscous oil (25.87 g). Purification by chromatography over silica (eluent: toluene) gave the product as a red-brown oil (3.825 g;15%). ##STR27## (b) 4-Pyrrolidino-2-naphthol

Provenance & Evidence