반응 #1450092

반응 방정식

4-ethyl-benzene-1,3-diol

naphthalen-2-yl-acetonitrile

boron trifluoride etherate

→

1-(5-ethyl-2,4-dihydroxy-phenyl)-2-naphthalen-2-yl-ethanone

반응 조건

후처리

1. 1
   기타was bubbled gaseous HCl for 12 h
2. 2
   기타The solids that formed
3. 3
   여과were collected by filtration
4. 4
   온도heated in 6N HCl (100 mL)
5. 5
   workup.ADDITIONThe mixture was diluted with water
6. 6
   추출extracted with CH2Cl2
7. 7
   추출The organic extract
8. 8
   세척was washed with water
9. 9
   기타dried
10. 10
    기타The oil obtained on concentration of the organic layer
11. 11
    기타was crystallized in EtOAc/hexanes

실험 절차

To a mixture of 4-ethyl-benzene-1,3-diol (a, 10 mmol) and naphthalen-2-yl-acetonitrile (b, 10 mmol) in boron trifluoride etherate (20 mL) was bubbled gaseous HCl for 12 h. The solids that formed were collected by filtration and heated in 6N HCl (100 mL) and EtOH (20 mL) for 6 h. The mixture was diluted with water and extracted with CH2Cl2. The organic extract was washed with water and dried. The oil obtained on concentration of the organic layer was crystallized in EtOAc/hexanes to give 1-(5-ethyl-2,4-dihydroxy-phenyl)-2-naphthalen-2-yl-ethanone (c, 0.74 g).

출처