Reacción #5596

Ecuación de reacción

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

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent removed on a rotary evaporator and water (50 ml)
2. 2
   workup.ADDITIONadded
3. 3
   Extracciónthe mixture was extracted with ethyl ether (3×75 ml)
4. 4
   Extracciónextracted with ethyl ether (2×50 ml)
5. 5
   Lavadothe combined organic extracts were washed with water (50 ml)
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe solvents removed
9. 9
   Otroleaving an oil, which
10. 10
    Otrowas purified by chromatography on silica
11. 11
    Otrorecrystallized from ethyl ether/Skellysolve B
12. 12
    Filtraciónfiltered
13. 13
    Otrothe product dried in vacuo at room temperature for 12 hours

Procedimiento

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.

Fuente