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

HRID 703104

Reaction equation

HRID 703104 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 (2.52 g, 0.045 mole) were added to a clear solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.57 g, 0.015 mole) and ethyl-4-bromobutyrate (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 extracted with ethyl ether (3×75 ml). The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl ether (2×50 ml), 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. extractionextracted with ethyl ether (3×75 ml)
  4. extractionextracted with ethyl ether (2×50 ml)
  5. washwashed with water (50 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents removed
  9. customleaving an oil, which
  10. customwas purified by chromatography on silica
  11. customrecrystallized from ethyl ether/Skellysolve B
  12. filtrationfiltered
  13. customthe product dried in vacuo at room temperature for 12 hours

Sources & evidence

ORD record
ord-20d220024dcc494d9d03b8ada752dfc9
Source dataset
uspto-grants-1991_01
Patent number
US04981853

Linked notes

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