반응 #55744

반응 방정식

sodium hydride

allyl bromide

2-hydroxy-benzoic acid ethyl ester

hydrobromic acid

2-hydroxy-benzoic acid

ethanol HCl

→

benzoic acid

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.DISTILLATIONThe dimethylformamide was then eliminated by distillation under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ether
4. 4
   세척washed with sodium hydroxide solution and water
5. 5
   농축the ether solution was concentrated by evaporation
6. 6
   온도by heating with 100 ml of 10% sodium hydroxide solution in the presence of a small amount of ethanol
7. 7
   온도After cooling
8. 8
   기타the substance that had precipitated
9. 9
   기타was re-precipitated from ammonia with the aid of charcoal
10. 10
    기타crystallized from dilute methanol

실험 절차

13.6 g of 4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-2-hydroxy-benzoic acid ethyl ester, M.p. 88°-89° C., (prepared by treatment of 4-(2-aminoethyl)-2-methoxy-benzoic acid. HCl with hydrobromic acid/glacial acetic acid, reaction of the resulting 4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-2-hydroxy-benzoic acid with ethanol/HCl) were dissolved in 75 ml of DMF and combined with 1.2 g of sodium hydride/80% strength in white oil. The whole was stirred for half an hour, 4.4 g of allyl bromide were added and stirring was continued for 4 hours at 65° C. The dimethylformamide was then eliminated by distillation under reduced pressure, the residue was dissolved in ether, washed with sodium hydroxide solution and water, the ether solution was concentrated by evaporation and the residue was hydrolyzed by heating with 100 ml of 10% sodium hydroxide solution in the presence of a small amount of ethanol. After cooling, the solution was acidified, the substance that had precipitated was re-precipitated from ammonia with the aid of charcoal and then crystallized from dilute methanol. The 2-allyloxy-4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-benzoic acid so obtained was found to melt at 122°-123° C.

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