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

HRID 563456Notes

Reaction equation

HRID 563456 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) dissolved in 100 mL of toluene, n-butyllithium (2.5 M in hexane, 3.6 mL) was slowly injected at −78° C. After stirring the mixture at ambient temperature for 12 hours, the reaction mixture was chilled to −78° C., and solution of (pentamethylcyclopentadienyl)titanium(IV) trichloride (2.5 g, 16.3 mmol) dissolved in 60 mL of toluene was slowly added thereto, and the reaction was continued at ambient temperature for 12 hours. When the reaction was completed, the reaction mixture was filtered through celite, and the solvent was removed. Recrystallization from purified toluene and hexane at −35° C., followed by filtration and drying under reduced pressure gave (dichloro) (pentamethylcyclopentadienyl) (1-phenylnaphthalen-2-yloxy)titanium(IV) (2.5 g) (yield: 58.2%) as red solid.

Workup

  1. customwas slowly injected at −78° C
  2. temperaturethe reaction mixture was chilled to −78° C.
  3. additionwas slowly added
  4. waitthe reaction was continued at ambient temperature for 12 hours
  5. filtrationthe reaction mixture was filtered through celite
  6. customthe solvent was removed
  7. customRecrystallization
  8. customfrom purified toluene and hexane at −35° C.
  9. filtrationfollowed by filtration
  10. customdrying under reduced pressure

Sources & evidence

ORD record
ord-72025fc055df4c0f8f1b111316d4f66a
Source dataset
uspto-grants-2011_11
Patent number
US08067511B2

Reaction notes

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