1-Phenylnaphthalen-2-ol → HCID 178425996, compound

HRID 387492Notes

Reaction equation

HRID 387492 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][C:8]=2[OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[Cl-:23].[Cl-:24].[Cl-].[CH3:26][C:27]1[C:31]([Ti+3:33])([CH3:32])[C:30]([CH3:34])=[C:29]([CH3:35])[C:28]=1[CH3:36]>C1(C)C=CC=CC=1>[Cl:23][Ti:33]([Cl:24])([C:31]1([CH3:32])[C:27]([CH3:26])=[C:28]([CH3:36])[C:29]([CH3:35])=[C:30]1[CH3:34])[O:17][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 112182821-Phenylnaphthalen-2-olHCID 178418339ButyllithiumHCID 178425990HCID 178425990, compound

Product 1

HCID 178425996HCID 178425996, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To solution of 1-phenylnaphthalen-2-ol (2.0 g, 9.1 mmol) in toluene (100 mL), slowly injected was n-butyllithium (2.5 M in hexane, 3.6 mL) at −78° C., and the mixture was stirred at ambient temperature for 12 hours. After chilling the reaction mixture to −78° C., slowly added was solution of (pentamethylcyclopentadienyl)titanium(IV) trichloride (2.5 g, 16.3 mmol) in toluene (60 mL), and the reaction was carried out at ambient temperature for 12 hours. When the reaction was completed, the reaction mixture was filtered through a celite filter, and solvent was removed therefrom. Recrystallization was carried out from purified toluene and hexane at −35° C. The solid was filtered and dried under reduced pressure to obtain (dichloro)(pentamethylcyclopentadienyl)(1-phenylnaphthalen-2-yloxy)titanium(IV) (2.5 g, yield: 58.2%) as red solid.

Workup

  1. customat −78° C.
  2. temperatureAfter chilling the reaction mixture to −78° C.
  3. additionslowly added
  4. waitthe reaction was carried out at ambient temperature for 12 hours
  5. filtrationthe reaction mixture was filtered through a celite
  6. filtrationfilter
  7. customsolvent was removed
  8. customRecrystallization
  9. customfrom purified toluene and hexane at −35° C
  10. filtrationThe solid was filtered
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-91c056dc4c8a41ac9c237cd1f9778e6a
Source dataset
uspto-grants-2013_02
Patent number
US08372996B2

Reaction notes

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