反応 #82878

反応方程式

triethylamine

2-Naphthol

naphthol

morpholine

chlorine

→

1-chloro-4-morpholino-2-naphthol

収率 109.5%

溶媒

toluene

toluene

反応条件

後処理

1. 1
   温度by warming
2. 2
   温度The pale brown solution was cooled
3. 3
   その他to precipitate
4. 4
   その他at 15°-20° C
5. 5
   ろ過The resulting brown mixture was filtered
6. 6
   その他to remove triethylamine hydrochloride as a white amorphous solid
7. 7
   洗浄The toluene filtrate was washed with water
8. 8
   その他dried
9. 9
   その他evaporated

実験手順

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

出典