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ChemicalBook CAS DataBase List UV-320
3846-71-7

UV-320 synthesis

10synthesis methods
NSC 373428

84755-44-2

UV-320

3846-71-7

The general procedure for the synthesis of 2-(2H-3,5-di-tert-butyl-2-hydroxyphenyl)benzotriazole from 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)benzotriazole N-oxide is as follows: Example 3: 10 g (0.03 mol) of 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)benzotriazole-N-oxide, 100 mg of palladium-carbon catalyst, 100 ml of solvent mixture of toluene and water (4:1 ratio by volume), and 3 g of 50% dimethylamine solution were added to a 500 ml autoclave equipped with a stirrer. After replacing the air in the autoclave with hydrogen, the hydrogen pressure was set to 10 kg/cm2. The temperature was raised to 50 °C with stirring, and the reaction was maintained at this temperature until no more hydrogen was absorbed by the mixture. After completion of the reaction, the autoclave was cooled and the catalyst was removed by filtration. A portion of the filtrate was quantitatively analyzed by GC and the yield of 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)benzotriazole was measured to be 85.6%. After removing the solvent from the filtrate by distillation, the residual solid was crystallized with ethanol and subsequently washed with ethanol to give 7.1 g of 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)benzotriazole (71% yield; melting point 152-155 °C).

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Yield:-

Steps:

Multi-step reaction with 3 steps
1: 2.) 1N HCl, sodium lauryl sulfate / 1.) diazotation, 2.) 45 deg C, 6 h
2: 91 percent / glucose, 2N NaOH / ethanol / 1 h / Heating
3: 79 percent / Zn, 2N NaOH / ethanol / 1 h / Ambient temperature

References:

Rosevear, Judi;Wilshire, John F. K. [Australian Journal of Chemistry,1982,vol. 35,# 10,p. 2089 - 2093]

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