Reaction #5596

Reaction equation

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

Solvents

acetone

Conditions

Workup

1. 1
   Otherthe solvent removed on a rotary evaporator and water (50 ml)
2. 2
   workup.ADDITIONadded
3. 3
   Extractionthe mixture was extracted with ethyl ether (3×75 ml)
4. 4
   Extractionextracted with ethyl ether (2×50 ml)
5. 5
   Washthe combined organic extracts were washed with water (50 ml)
6. 6
   Dryingdried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Otherthe solvents removed
9. 9
   Otherleaving an oil, which
10. 10
    Otherwas purified by chromatography on silica
11. 11
    Otherrecrystallized from ethyl ether/Skellysolve B
12. 12
    Filtrationfiltered
13. 13
    Otherthe product dried in vacuo at room temperature for 12 hours

Procedure

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.

Source