反応 #82875

反応方程式

chlorine

2-Naphthol

piperidine

triethylamine

naphthol

→

1-chloro-4-piperidino-2-naphthol

収率 91.0%

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 in 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 (210 ml) by warming. The pale brown solution was cooled and vigorously stirred until the naphthol began to precipitate and chlorine (30.20 g;0.425 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 piperidine (19.55 g;0.230 mol), in toluene (210 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 in water, dried and evaporated to give 1-chloro-4-piperidino-2-naphthol (of structure 3a below) as a brown viscous oil (61.80 g;77% purity by gel permeation chromatography;91% yield based on 2-naphthol). Distillation gave the naphthol as a viscous amber gum B.Pt 150° C./0.3 mmHg. ##STR15## (b) 4-Piperidino-2-naphthol

出典