반응 #1880956

반응 방정식

methyl bromoacetate

methyl bromoacetate

ether

sodium methoxide

4-allylcatechol

sodium methoxide

methyl bromoacetate

→

methyl 4-allyl-2-(ethoxycarbonylmethoxy)phenoxyacetate

수율 65.0%

용매

methanol

반응 조건

후처리

1. 1
   온도After refluxing for 8 h
2. 2
   온도after a further 4 h of heating
3. 3
   온도After a further 4 h under reflux
4. 4
   여과filtering off the precipitate
5. 5
   기타formed
6. 6
   농축The filtrate was concentrated on a rotary evaporator
7. 7
   기타The organic phase was separated off
8. 8
   추출the aqueous phase was extracted three times
9. 9
   건조The combined organic phases were dried over sodium sulfate
10. 10
    농축concentrated to dryness on a rotary evaporator

실험 절차

12.8 g (225 mmol) of 95% pure sodium methoxide were introduced into a solution of 16.8 g (112 mmol) of 4-allylcatechol in 250 ml of methanol, with stirring, followed by 21 ml (225 mmol) of methyl bromoacetate. After refluxing for 8 h, a further 21 ml (225 mmol) of methyl bromoacetate were added, and, after a further 4 h of heating, a further 12.8 g (225 mmol) of sodium methoxide and a further 21 ml (225 mmol) of methyl bromoacetate. After a further 4 h under reflux, the mixture was worked up by adding 500 ml of ether and filtering off the precipitate formed. The filtrate was concentrated on a rotary evaporator and taken up in ether/water/saturated ammonium chloride solution (1:1:1). The organic phase was separated off, and the aqueous phase was extracted three times, each time with 200 ml of ether. The combined organic phases were dried over sodium sulfate and concentrated to dryness on a rotary evaporator. After flash chromatography (ether/pentane, 1:1, Rf=0.35) on silica gel, 21.4 g (65%) of methyl 4-allyl-2-(ethoxycarbonylmethoxy)phenoxyacetate were obtained.

출처