Sodium hydride → HCID 178425994, compound

HRID 658228Notes

Reaction equation

HRID 658228 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]=1[OH:16])([CH3:3])[CH3:2].[H-].[Na+].[Cl:19][Ti:20](Cl)([Cl:31])[C:21]1([CH3:30])[C:25]([CH3:26])=[C:24]([CH3:27])[C:23]([CH3:28])=[C:22]1[CH3:29]>C1(C)C=CC=CC=1>[Cl:19][Ti:20]([Cl:31])([C:21]1([CH3:30])[C:22]([CH3:29])=[C:23]([CH3:28])[C:24]([CH3:27])=[C:25]1[CH3:26])[O:16][C:5]1[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 227315083-(Propan-2-yl)[1,1'-biphenyl]-2-olHCID 178425993HCID 178425993, compound

Product 1

HCID 178425994HCID 178425994, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

700 mg (3.28 mmol) of 2-isopropyl-6-phenylphenol and 236 mg (9.84 mmol) of sodium hydride were dissolved in 10 ml of toluene, and then refluxed for 4 hours. The refluxed solution was cooled to room temperature, and then a solution of 930 mg (3.21 mmol) of trichloro(pentamethylcyclopentadienyl)titanium (IV) was slowly added dropwise thereto, and the mixture was refluxed for 24 hours. After completion of the reflux reaction, volatile components were removed from the reaction solution, and the residue was washed with purified hexane, recrystallized from a mixed solvent of toluene/hexane −35° C., filtered, and then dried in a vacuum, thus obtaining 1.0 g of a red solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperaturethe mixture was refluxed for 24 hours
  3. customAfter completion of the reflux reaction, volatile components
  4. customwere removed from the reaction solution
  5. washthe residue was washed with purified hexane
  6. customrecrystallized from a mixed solvent of toluene/hexane −35° C.
  7. filtrationfiltered
  8. customdried in a vacuum

Sources & evidence

ORD record
ord-b5dec4770b60422a9a5c464dd8673ed0
Source dataset
uspto-grants-2011_12
Patent number
US08076428B2

Reaction notes

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