Water → Butanoic acid, 4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-

HRID 1614538Notes

Reaction equation

HRID 1614538 reaction equation
[OH-].[K+].[CH3:3][C:4]([C:7]1[CH:12]=[C:11]([SH:13])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:6])[CH3:5].C([O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br)C.O>CC(C)=O>[CH3:6][C:4]([C:7]1[CH:12]=[C:11]([S:13][CH2:25][CH2:24][CH2:23][C:22]([OH:27])=[O:21])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:3])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 9840255Butanoic acid, 4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium hydroxide flakes (2.52g, 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, extraced 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.

Workup

  1. customthe solvent removed on a rotary evaporator and water (50 ml)
  2. additionadded
  3. extractionthe mixture was extracted with ethyl ether (3×75 ml)
  4. washthe combined organic extracts were washed with water (50 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents removed
  8. customleaving an oil, which
  9. customwas purified by chromatography on silica
  10. customrecrystallized from ethyl ether/Skellysolve B
  11. filtrationfiltered
  12. customthe product dried in vacuo at room temperature for 12 hours

Sources & evidence

ORD record
ord-f397f7a02bd147388e4eb5c954461967
Source dataset
uspto-grants-1993_03
Patent number
US05198435

Reaction notes

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