반응 #43940

반응 방정식

chloromethyl methyl ether

4-bromo-3,5-dimethylphenol

hexane

sodium hydride

→

title compound

수율 74.0%

2-bromo-5-(methoxymethoxy)-1,3-dimethylbenzene

수율 74.0%

용매

tetrahydrofuran

sodium hydroxide

반응 조건

후처리

1. 1
   기타the supernatant was removed
2. 2
   workup.ADDITIONTetrahydrofuran (460 mL) was added
3. 3
   workup.ADDITIONAfter completion of the dropwise addition
4. 4
   workup.STIRRINGthe mixture was stirred at 0° C. for 10 min
5. 5
   온도to warm to room temperature
6. 6
   workup.STIRRINGwas stirred for 20 min
7. 7
   workup.STIRRINGthe mixture was stirred for 24 hr
8. 8
   기타Tetrahydrofuran was evaporated under reduced pressure
9. 9
   추출the residue was extracted with diethyl ether
10. 10
    세척The extract was washed successively with 2 M aqueous sodium hydroxide solution and saturated brine
11. 11
    건조dried over anhydrous magnesium sulfate
12. 12
    농축concentrated under reduced pressure
13. 13
    기타The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-10:90)

실험 절차

Under nitrogen atmosphere, hexane (50 mL) was added to sodium hydride (50% in oil, 12.6 g, 264 mmol). The mixture was stirred for 30 sec, and stood still, and the supernatant was removed. Tetrahydrofuran (460 mL) was added thereto, and the mixture was cooled to 0° C. A solution of 4-bromo-3,5-dimethylphenol (53.0 g, 264 mmol) in tetrahydrofuran (50 mL) was added slowly dropwise. After completion of the dropwise addition, and the mixture was stirred at 0° C. for 10 min, allowed to warm to room temperature, and was stirred for 20 min. Then, chloromethyl methyl ether (22.3 g, 277 mmol) was added slowly at room temperature, and the mixture was stirred for 24 hr. The reaction mixture was diluted with 1 M aqueous sodium hydroxide solution (80 mL). Tetrahydrofuran was evaporated under reduced pressure, and the residue was extracted with diethyl ether. The extract was washed successively with 2 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-10:90) to give the title compound (47.6 g, yield 74%) as a colorless oil.

출처