반응 #82878

반응 방정식

triethylamine

2-Naphthol

naphthol

morpholine

chlorine

→

1-chloro-4-morpholino-2-naphthol

수율 109.5%

용매

toluene

toluene

반응 조건

후처리

1. 1
   온도by warming
2. 2
   온도The pale brown solution was cooled
3. 3
   기타to precipitate
4. 4
   기타at 15°-20° C
5. 5
   여과The resulting brown mixture was filtered
6. 6
   기타to remove triethylamine hydrochloride as a white amorphous solid
7. 7
   세척The toluene filtrate was washed with water
8. 8
   기타dried
9. 9
   기타evaporated

실험 절차

2-Naphthol (28.8 g; 0.200 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 (31.29 g;0.442 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 (24.68 g;0.244 mol) in one portion and then with a solution of morpholine (17.40 g;0.20 mol) in toluene (180 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-morpholino-2-naphthol as a brown viscous oil (57.76 g). Purification by chromatography over silica (eluent: 15% ethyl acetate in toluene) gave the product as an off-white solid (34.37 g;65%). Further purification by crystallisation from toluene gave the product as a white solid, m.pt. 163°-65° C. ##STR18## (b) 4-Morpholino-2-naphthol

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