反応 #54513

反応方程式

5-chloro-2-dodecyl-1,4-naphthoquinone

sodium carbonate

potassium hydroxide

hydrochloric acid

hydrogen peroxide

→

5-chloro-2-dodecyl-3-hydroxy-1,4-naphthoquinone

溶媒

water

ethanol

ethanol

反応条件

後処理

1. 1
   温度refluxed for 10 minutes
2. 2
   温度The resulting deep red mixture was then heated to 50° C. over 25 minutes
3. 3
   温度After cooling to 10° C. the mixture
4. 4
   ろ過The resulting yellow crystals were filtered
5. 5
   その他dried
6. 6
   その他purified by column chromatography on silica gel
7. 7
   その他Solvent removal

実験手順

A mixture of 1.7 parts of 5-chloro-2-dodecyl-1,4-naphthoquinone, 25 parts ethanol, 0.626 parts anhydrous sodium carbonate and 6.3 parts water was contacted with 1.13 parts of 30% hydrogen peroxide at 32° C. and then refluxed for 10 minutes. The resulting mixture was then cooled to 50° C. and a solution of 1.56 parts of potassium hydroxide in 49.5 parts of ethanol was added to it. The resulting deep red mixture was then heated to 50° C. over 25 minutes and the temperature held there for 45 minutes. After cooling to 10° C. the mixture was then contacted with 251 parts of 2.72% hydrochloric acid. The resulting yellow crystals were filtered, dried and purified by column chromatography on silica gel using 1-chlorobutane as eluent. Solvent removal gave 1.4 parts of 5-chloro-2-dodecyl-3-hydroxy-1,4-naphthoquinone, m.p. 102°-104.5° C.

出典