تفاعل #5596

معادلة التفاعل

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

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solvent removed on a rotary evaporator and water (50 ml)
2. 2
   workup.ADDITIONadded
3. 3
   استخلاصthe mixture was extracted with ethyl ether (3×75 ml)
4. 4
   استخلاصextracted with ethyl ether (2×50 ml)
5. 5
   غسيلthe combined organic extracts were washed with water (50 ml)
6. 6
   تجفيفdried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىthe solvents removed
9. 9
   أخرىleaving an oil, which
10. 10
    أخرىwas purified by chromatography on silica
11. 11
    أخرىrecrystallized from ethyl ether/Skellysolve B
12. 12
    ترشيحfiltered
13. 13
    أخرىthe product dried in vacuo at room temperature for 12 hours

الإجراء التجريبي

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.

المصدر