반응 #45538

반응 방정식

4,4′-dichloro-benzophenone

potassium hydroxide

hydrochloric acid

3-tert-butyl-1-methyl-cyclopentadiene

→

aimed compound

3-tert-butyl-1-methyl-6,6-di(4-chloro-phenyl)fulvene

용매

Diethyl ether

dimethoxy ethane

반응 조건

후처리

1. 1
   기타In a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock
2. 2
   workup.ADDITIONwere added in a nitrogen atmosphere
3. 3
   온도under reflux for 3 days
4. 4
   workup.ADDITIONthe reaction mixture was gradually added dropwise
5. 5
   workup.STIRRINGstirred for some time
6. 6
   기타to separate an organic phase
7. 7
   세척The organic phase was washed with a saturated sodium bicarbonate aqueous solution, water and saturated brine
8. 8
   건조The organic phase was dried with anhydrous magnesium sulfate
9. 9
   여과the drying agent was filtered off
10. 10
    workup.DISTILLATIONthe solvent was distilled off from the filtrate under reduced pressure
11. 11
    기타to give a reddish-orange solid
12. 12
    기타The solid was purified with a column chromatography
13. 13
    workup.DISTILLATIONthe developing solvent was distilled off under reduced pressure

실험 절차

In a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock thoroughly purged with nitrogen, 0.65 g of powdery potassium hydroxide (13.0 mmol) and 70 ml of dehydrated dimethoxy ethane were added in a nitrogen atmosphere. To the suspension, 1.24 g of 3-tert-butyl-1-methyl-cyclopentadiene (9.11 mmol) was added dropwise at room temperature and then 2.40 g of 4,4′-dichloro-benzophenone (9.58 mmol) was added and stirred under reflux for 3 days. To a 30 ml of a hydrochloric acid aqueous solution (1N) set in an ice bath, the reaction mixture was gradually added dropwise and stirred for some time. Diethyl ether was added to the mixed solution to separate an organic phase. The organic phase was washed with a saturated sodium bicarbonate aqueous solution, water and saturated brine. The organic phase was dried with anhydrous magnesium sulfate, thereafter the drying agent was filtered off and the solvent was distilled off from the filtrate under reduced pressure to give a reddish-orange solid. The solid was purified with a column chromatography using 110 g of silica gel (developing solvent: n-hexane) and the developing solvent was distilled off under reduced pressure, and thereby the aimed compound was obtained in an amount of 2.79 g (7.56 mmol) as a red solid (yield: 83%).

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