Sodium hydride → HCID 178425994, compound

HRID 563452Notes

Reaction equation

HRID 563452 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 1140TolueneSolvent2×

Procedure

Solution of 2-isopropyl-6-phenylphenol (700 mg, 3.28 mmol) and sodium hydride (236 mg, 9.84 mmol) in toluene (10 mL) was subjected to reaction under reflux for 4 hours. Then, the mixture was cooled to ambient temperature, and solution of (trichloro)(pentamethylcyclopentadienyl)titanium (IV) (930 mg, 3.21 mmol) dissolved in toluene (5 mL) was slowly added dropwise thereto. The resultant mixture was reacted under reflux for 24 hours. When the reaction was completed, volatile substances were removed therefrom, and the residue was washed with purified hexane. Recrystallization from toluene/hexane mixed solvent at −35° C., followed by filtration and drying under reduced pressure gave red solid (1.0 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. additionwas slowly added dropwise
  3. temperatureunder reflux for 24 hours
  4. customvolatile substances were removed
  5. washthe residue was washed with purified hexane
  6. customRecrystallization from toluene/hexane mixed solvent at −35° C.
  7. filtrationfollowed by filtration
  8. customdrying under reduced pressure

Sources & evidence

ORD record
ord-0a7d6003041348fe8d32aa94d635b840
Source dataset
uspto-grants-2011_11
Patent number
US08067511B2

Reaction notes

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