반응 #95252

반응 방정식

calcium carbonate

calcium carbonate

1-acetoxy-2-(5-acetoxy-pentyl)-1-cyclopentene

1-acetoxy-2-(5-acetoxypentyl)-1-cyclopentene

bromine

water

→

2-(5-acetoxypentyl)-2-cyclopentenone

용매

N,N-dimethylacetamide

carbon tetrachloride

chloroform

반응 조건

후처리

1. 1
   workup.ADDITIONmixture of 405 g
2. 2
   workup.ADDITIONis added simultaneously 1016 g
3. 3
   workup.STIRRINGThe mixture is stirred for half an hour
4. 4
   workup.ADDITIONafter addition of the reagents
5. 5
   기타the phases are then separated
6. 6
   세척The organic phase is washed with 2% sodium thiosulfate solution, water, and saturated brine
7. 7
   건조dried (MgSO4)
8. 8
   기타evaporated in vacuo to an oil
9. 9
   workup.ADDITIONThe oil is immediately added to a refluxing slurry of 500 g
10. 10
    온도The mixture is cooled
11. 11
    여과filtered
12. 12
    기타partitioned between water and diethyl ether
13. 13
    세척The organic phase is washed with water and saturated brine
14. 14
    건조dried (MgSO4)
15. 15
    기타evaporated
16. 16
    기타to yield 757 g

실험 절차

To a well stirred mixture of 405 g. (4.05 moles) of calcium carbonate, 3 l. of water, and 2.5 l. of chloroform cooled to 5° C. is added simultaneously 1016 g. (4.0 moles) of 1-acetoxy-2-(5-acetoxy-pentyl)-1-cyclopentene (Example 56) and a solution of 648 g. (4.05 moles) of bromine in 500 ml. of carbon tetrachloride at a rate to maintain a temperature below 10° C. The mixture is stirred for half an hour after addition of the reagents and the phases are then separated. The organic phase is washed with 2% sodium thiosulfate solution, water, and saturated brine, dried (MgSO4), and evaporated in vacuo to an oil. The oil is immediately added to a refluxing slurry of 500 g. (5.0 moles) of calcium carbonate in 2.5 l of N,N-dimethylacetamide under nitrogen and the mixture is then refluxed for thirty minutes. The mixture is cooled, filtered, and partitioned between water and diethyl ether. The organic phase is washed with water and saturated brine, dried (MgSO4), and evaporated to yield 757 g. of an oil, b.p. 116°-118° C. (0.25 mm.).

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