p-Toluenesulfonic acid → 3,3',6,6'-Tetramethyl-2,2'-biphenol

HRID 2297083Notes

Reaction equation

HRID 2297083 reaction equation
C([C:5]1[C:10]([CH3:11])=[C:9]([OH:12])[C:8]([C:13]2[C:14]([OH:25])=[C:15]([CH3:24])[C:16](C(C)(C)C)=[CH:17][C:18]=2[CH3:19])=[C:7]([CH3:26])[CH:6]=1)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:19][C:18]1[CH:17]=[CH:16][C:15]([CH3:24])=[C:14]([OH:25])[C:13]=1[C:8]1[C:9]([OH:12])=[C:10]([CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:26]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 185446495,5'-Bis(t-butyl)-3,3',6,6'-tetramethyl-2,2'-biphenol

Product 1

HCID 113569233,3',6,6'-Tetramethyl-2,2'-biphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 mL flask were added 0.5 g of 5,5′-Bis(t-butyl)-3,3′,6,6′-tetramethyl-2,2′-biphenol, 5 mL of xylenes and 0.05 g of p-toluenesulfonic acid. The mixture was refluxed for about 2 hours. The mixture was cooled and water added. The mixture was extracted with hexanes; the organic layer was washed with water and dried over MgSO4. After removing the solvent, the residue was recrystallized from petroleum ether.

Workup

  1. temperatureThe mixture was refluxed for about 2 hours
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with hexanes
  4. washthe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customAfter removing the solvent
  7. customthe residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-35a99cd3e2f24e8699bdfde0ecadada8
Source dataset
uspto-grants-2002_12
Patent number
US06489517B1

Reaction notes

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