반응 #2006436

반응 방정식

1-ethyl-2-methoxycyclohexanol

n-butyllithium

hexane

methacryloyl chloride

→

1-ethyl-2-methoxycyclohexyl methacrylate

용매

—

ice water

ether

ether

반응 조건

후처리

1. 1
   기타equipped with a water condenser, addition funnel and a nitrogen inlet
2. 2
   온도This solution was cooled in an ice/water bath
3. 3
   온도heated
4. 4
   온도to reflux for 30 minutes
5. 5
   온도The reaction mixture was cooled to room temperature
6. 6
   기타quenched with 125 ml of deionized water
7. 7
   기타The organic phase was separated
8. 8
   추출the water phase was extracted with 50 ml ether
9. 9
   세척The combined ether solutions were washed with 100 ml brine
10. 10
    건조dried over anhydrous magnesium sulfate
11. 11
    기타The solvent was removed in a rotary evaporator
12. 12
    기타the crude product was chromatographed on a neutral alumina column

실험 절차

1-ethyl-2-methoxycyclohexanol from the previous step (10 g, 0.063 mole) in 50 ml ether was placed in a three neck flask equipped with a water condenser, addition funnel and a nitrogen inlet. This solution was cooled in an ice/water bath and n-butyllithium, 1.6 molar in hexane (45 ml, 0.072 mole) was added dropwise. The contents were allowed to warm to room temperature and stirred for 30 minutes. The mixture was cooled again in ice/water bath and methacryloyl chloride (7.31 g, 0.070 mole) in 25 ml ether was added dropwise and heated to reflux for 30 minutes. The reaction mixture was cooled to room temperature and quenched with 125 ml of deionized water. The organic phase was separated and the water phase was extracted with 50 ml ether. The combined ether solutions were washed with 100 ml brine and dried over anhydrous magnesium sulfate. The solvent was removed in a rotary evaporator and the crude product was chromatographed on a neutral alumina column using hexane as elutant. The product was a clear liquid (9.79 g) which was characterized by NMR and IR.

출처