반응 #59776

반응 방정식

2-hydroxy-5-bromo-phenylacetic acid

potassium tert.butoxide

benzylbromide

→

2-benzyloxy-5-bromo-phenylacetic acid

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONpoured onto ice water
2. 2
   추출extracted with ethyl acetate
3. 3
   기타The combined organic extracts are dried
4. 4
   기타evaporated down
5. 5
   workup.DISSOLUTIONThe residue is dissolved in 100 ml of ethanol
6. 6
   workup.ADDITIONafter the addition of 50 ml of 2N sodium hydroxide solution
7. 7
   workup.STIRRINGstirred for 3 hours at ambient temperature
8. 8
   workup.DISTILLATIONThe solvent is distilled off
9. 9
   추출After extraction with ethyl acetate the organic phases
10. 10
    기타are dried
11. 11
    기타evaporated down
12. 12
    기타The residue is chromatographed on silica gel
13. 13
    세척eluted with petroleum ether/ethyl acetate (8:2)

실험 절차

A solution of 12.4 g (0.053 mol) of 2-hydroxy-5-bromo-phenylacetic acid in 125 ml of dimethylformamide is combined with 14 g (0.125 mol) of potassium tert.butoxide. After 15 minutes at ambient temperature 18.5 g (0.108 mol) of benzylbromide are added. The reaction solution is stirred for 3 hours at ambient temperature, poured onto ice water and extracted with ethyl acetate. The combined organic extracts are dried and evaporated down. The residue is dissolved in 100 ml of ethanol and after the addition of 50 ml of 2N sodium hydroxide solution stirred for 3 hours at ambient temperature. The solvent is distilled off, the residue is adjusted to pH 4 with 2N hydrochloric acid. After extraction with ethyl acetate the organic phases are dried and evaporated down. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (8:2).

출처