ChemicalBook CAS DataBase List 4-Epoxypropanoxycarbazole

4-Epoxypropanoxycarbazole synthesis

5synthesis methods

Product Name:4-Epoxypropanoxycarbazole
CAS Number:51997-51-4
Molecular formula:C15H13NO2
Molecular Weight:239.27

52602-39-8 Synthesis

52602-39-8
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106-89-8 Synthesis

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51997-51-4
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Yield:51997-51-4 80.4%

Reaction Conditions:

Stage #1:9H-carbazol-4-ol with sodium hydroxide in water;isopropyl alcohol at 23 - 28; for 1 h;
Stage #2:epichlorohydrin in water;isopropyl alcohol at 20 - 40; for 15 - 20 h;

Steps:

1
200.Og (1.09 mole) of 4- hydroxy carbazole is dissolved in 500.0 ml of isopropyl alcohol. To this solution is added dropwise an aqueous solution of sodium hydroxide made from 48 g (1.2 moles) of sodium hydroxide dissolved in 700.0 ml of water. The addition of alkali solution is done by maintaining the temperature at 23 to 28 °C. After the addition of entire quantity of sodium hydroxide solution, the reaction mixture is stirred for 1 hour at the same temperature of 23 to 28 °C. To this solution 236 g (2.55 moles) of epichlorhydrin is added all at once. The reaction mixture is then stirred at room temperature (30-40°C) for 15-20 hours. During this period the reaction mixture is monitored by thin layer chromatography (TLC), till the reaction showed complete utilization of 4-hydroxy carbazole. 4- (2,3-epoxypropoxy) thus formed, precipitated from the reaction mixture, which is filtered and the cake is washed with 150ml of water and 150 ml of isopropyl alcohol. The product is dried at 50-55 °C for 4-5 hours. Yield: 210.0 g. (80.4%) M. P. 133 °c ¹H NMR (200 MHZ, in CDCl3) 8 (ppm) 8.1 (bs, 1H, exchanges with d20), 6.8-8.3 (m 7H), 4.4-4.2 (m, 2H), 3.5 (m, 1H), 2.8-3 (m, 2H)

References:

USV LIMITED WO2005/115981, 2005, A2 Location in patent:Page/Page column 10

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52602-39-8 Synthesis

52602-39-8
428 suppliers
$8.00/5g