반응 #5596

반응 방정식

Water

Potassium hydroxide

2,6-bis(1,1-dimethylethyl)-4-mercaptophenol

ethyl-4-bromo-butyrate

→

4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxy phenyl]thio]butanoic acid

용매

acetone

반응 조건

후처리

1. 1
   기타the solvent removed on a rotary evaporator and water (50 ml)
2. 2
   workup.ADDITIONadded
3. 3
   추출the mixture was extracted with ethyl ether (3×75 ml)
4. 4
   추출extracted with ethyl ether (2×50 ml)
5. 5
   세척the combined organic extracts were washed with water (50 ml)
6. 6
   건조dried over sodium sulfate
7. 7
   여과filtered
8. 8
   기타the solvents removed
9. 9
   기타leaving an oil, which
10. 10
    기타was purified by chromatography on silica
11. 11
    기타recrystallized from ethyl ether/Skellysolve B
12. 12
    여과filtered
13. 13
    기타the product dried in vacuo at room temperature for 12 hours

실험 절차

Potassium hydroxide flakes (2.52 g, 0.045 mole) were added to a clear solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.57 g, 0.0165 mole) and ethyl-4-bromo-butyrate (3.23 g, 0.0165 mole) in acetone (10 ml). Water (20 ml) was added and the solution stirred for 1.5 hours, the solvent removed on a rotary evaporator and water (50 ml) added, and the mixture was extracted with ethyl ether (3×75 ml). The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl ether (2×50 ml), the combined organic extracts were washed with water (50 ml), dried over sodium sulfate, filtered and the solvents removed, leaving an oil, which was purified by chromatography on silica, recrystallized from ethyl ether/Skellysolve B, filtered and the product dried in vacuo at room temperature for 12 hours, m.p. ca. 112°-113.5° C.

출처