반응 #1331385

반응 방정식

4-methylcatechol

1,2-dibromoethane

K2CO3

→

title intermediate

수율 50.0%

6-methyl-1,4-benzodioxane

수율 50.0%

용매

ethylene glycol

반응 조건

후처리

1. 1
   온도to cool to ambient temperature
2. 2
   여과After the mixture was filtered through celite
3. 3
   workup.ADDITIONthe solution was diluted with brine (800 mL)
4. 4
   추출extracted with organic solvents (CH2Cl2/hexane/EtOAc: 1:3:1,3×500 mL)
5. 5
   건조The organic layer was dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to provide a crude oil
9. 9
   세척Flash silica gel chromatography eluting with hexane (100%) gradient to ether/hexane (8:2)

실험 절차

A mixture of 4-methylcatechol (33.04 g, 266.1 mmol), 1,2-dibromoethane (100 g, 532.3 mmol), K2CO3 (75.4 g, 545.5 mmol) and sodium iodide (0.2 g, 1.33 mmol) in ethylene glycol (500 mL) was heated to 130° C. under nitrogen for five hours. The solution was allowed to cool to ambient temperature and stirred overnight. After the mixture was filtered through celite, the solution was diluted with brine (800 mL) and extracted with organic solvents (CH2Cl2/hexane/EtOAc: 1:3:1,3×500 mL). The organic layer was dried over Na2SO4, filtered and concentrated to provide a crude oil. Flash silica gel chromatography eluting with hexane (100%) gradient to ether/hexane (8:2) afforded the title intermediate as a colorless oil 20.0 g (50%).

출처