反応 #54511

反応方程式

1-(5-chloro-1-hydroxynaphthalen-2-yl)-1-dodecanone

hydrochloric acid

hydrochloric acid

→

5-chloro-2-dodecyl-1-naphthalenol

溶媒

ethanol

反応条件

後処理

1. 1
   洗浄by washing with ethanol
2. 2
   workup.ADDITIONThe zinc amalgam was added in small portions throughout the reaction period
3. 3
   温度Upon cooling
4. 4
   その他a solid separated
5. 5
   workup.DISSOLUTIONAfter dissolution of this solid in ethanol
6. 6
   ろ過zinc amalgam was filtered
7. 7
   温度cooling
8. 8
   その他gave 0.5 parts of starting material which
9. 9
   ろ過was filtered
10. 10
    その他Concentration of the filtrate, purification
11. 11
    その他by recrystallization from ethanol, and column chromatography on silica gel

実験手順

A solution of 17.4 parts of 1-(5-chloro-1-hydroxynaphthalen-2-yl)-1-dodecanone and 107 parts of 37% hydrochloric acid in 2.5 parts of ethanol was contacted with stirring at reflux during 26 hours, with 40 parts of zinc dust which has been amalgamated by treatment with 3 parts of mercuric chloride and 53 parts of 2.1% hydrochloric acid followed by washing with ethanol. The zinc amalgam was added in small portions throughout the reaction period. Upon cooling, a solid separated. After dissolution of this solid in ethanol, zinc amalgam was filtered, and cooling gave 0.5 parts of starting material which was filtered. Concentration of the filtrate, purification by recrystallization from ethanol, and column chromatography on silica gel using 1-chlorobutane as eluent gave 12 parts of 5-chloro-2-dodecyl-1-naphthalenol, m.p. 68°-70° C.

出典