反応 #5596

反応方程式

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

溶媒

acetone

反応条件

後処理

1. 1
   その他the solvent removed on a rotary evaporator and water (50 ml)
2. 2
   workup.ADDITIONadded
3. 3
   抽出the mixture was extracted with ethyl ether (3×75 ml)
4. 4
   抽出extracted with ethyl ether (2×50 ml)
5. 5
   洗浄the combined organic extracts were washed with water (50 ml)
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   その他the solvents removed
9. 9
   その他leaving an oil, which
10. 10
    その他was purified by chromatography on silica
11. 11
    その他recrystallized from ethyl ether/Skellysolve B
12. 12
    ろ過filtered
13. 13
    その他the product dried in vacuo at room temperature for 12 hours

実験手順

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.

出典