반응 #50101

반응 방정식

alcohol

2,2,6-trichloro-6-fluorocyclohexanol

acetone

→

alcohol

수율 32.0%

2,2,6-trichloro-6-fluorocyclohexanol

수율 32.0%

diol

2,2,6-trichloro-6-fluoro-1,1-cyclohexane-diol

반응 조건

후처리

1. 1
   기타fitted with a condenser and with magnetic stirring
2. 2
   workup.ADDITION5 cm3 of the Jones reactant were introduced gently
3. 3
   온도the reaction mixture was then heated to 45°-50° C. for 16 h
4. 4
   workup.ADDITION(1 cm3 of Jones reactant having been added after 4 h and 2 cm3 after 9 h of reaction)
5. 5
   기타At the end of reaction the Jones reactant
6. 6
   기타was destroyed with 10 cm3 of isopropanol
7. 7
   workup.ADDITIONthe mixture was diluted with 10 cm3 of water
8. 8
   추출extracted with dichloromethane
9. 9
   건조dried over magnesium sulfate
10. 10
    기타the solvents were evaporated off
11. 11
    기타purified by flash chromatography

실험 절차

0.5 g (2.26 mmol) of alcohol 1b in solution in 3 cm3 of acetone were introduced into a 10-cm3 round bottom flask fitted with a condenser and with magnetic stirring. 5 cm3 of the Jones reactant were introduced gently; the reaction was highly exothermic; the reaction mixture was then heated to 45°-50° C. for 16 h (1 cm3 of Jones reactant having been added after 4 h and 2 cm3 after 9 h of reaction). At the end of reaction the Jones reactant was destroyed with 10 cm3 of isopropanol, the mixture was diluted with 10 cm3 of water, extracted with dichloromethane and dried over magnesium sulfate, and the solvents were evaporated off. The material was incorporated onto silica and purified by flash chromatography. 0.16 g of starting alcohol 1b (32%) and 0.30 g of pure diol 3a were isolated, that was a 56% yield of compound 3a (Yld based on the unrecovered alcohol 1b=85%).

출처