2,6-Di-tert-butylphenol → HCID 178425998, compound

HRID 1172149Notes

Reaction equation

HRID 1172149 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[Cl:21][Ti:22](Cl)([Cl:33])[C:23]1([CH3:32])[C:27]([CH3:28])=[C:26]([CH3:29])[C:25]([CH3:30])=[C:24]1[CH3:31]>C(OCC)C>[Cl:21][Ti:22]([Cl:33])([C:23]1([CH3:32])[C:24]([CH3:31])=[C:25]([CH3:30])[C:26]([CH3:29])=[C:27]1[CH3:28])[O:15][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][C:7]=1[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 314052,6-Di-tert-butylphenolHCID 178418339ButyllithiumHCID 178425993HCID 178425993, compound

Product 1

HCID 178425998HCID 178425998, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

After 600 mg of 2,6-di-tert-butylphenol (2.91 mmol) (Aldrich, 99%) were dissolved in 30 mL of diethylether, 1.28 mL of butyl lithium (2.5 M hexane solution) were slowly dropped thereonto at −31° C. After 1 hour, agitation was conducted at normal temperature for 6 hours. The resulting mixture was dissolved in diethylether, and a solution in which (trichloro)(pentamethylcyclopentadienyl)titanium(IV) (752 mg, 2.60 mmol) was dissolved in 10 mL of diethylether was slowly dropped thereonto at −30° C. After 1 hour, agitation was conducted at normal temperature for 6 hours. The solvent was removed from the resulting product, and the solvent-free product was dissolved in 10 mL of toluene and then recrystallized to produce 829 mg of red solid component.

Workup

  1. customat −31° C
  2. waitagitation was conducted at normal temperature for 6 hours
  3. additionwas slowly dropped
  4. customat −30° C
  5. waitAfter 1 hour
  6. waitagitation was conducted at normal temperature for 6 hours
  7. customThe solvent was removed from the resulting product
  8. dissolutionthe solvent-free product was dissolved in 10 mL of toluene
  9. customrecrystallized

Sources & evidence

ORD record
ord-2b334a5084bd4a3988c69641c1d4e7a1
Source dataset
uspto-grants-2010_11
Patent number
US07833926B2

Reaction notes

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