Sodium hydride → HCID 178425995, compound

HRID 733023Notes

Reaction equation

HRID 733023 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([OH:14])=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:3]=1.[H-].[Na+].[Cl:23][Ti:24](Cl)([Cl:35])[C:25]1([CH3:34])[C:29]([CH3:30])=[C:28]([CH3:31])[C:27]([CH3:32])=[C:26]1[CH3:33]>C1(C)C=CC=CC=1>[Cl:23][Ti:24]([Cl:35])([C:25]1([CH3:34])[C:26]([CH3:33])=[C:27]([CH3:32])[C:28]([CH3:31])=[C:29]1[CH3:30])[O:14][C:5]1[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3][C:2]([CH3:1])=[CH:7][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109232754-methyl-2,6-diphenylphenolHCID 178425993HCID 178425993, compound

Product 1

HCID 178425995HCID 178425995, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4-methyl-2,6-diphenylphenol (400 mg, 1.53 mmol) and sodium hydride (110 mg, 4.60 mmol) were dissolved in 10 mL of toluene, and then refluxed for 4 hours. Subsequently, cooling to normal temperature was conducted, a solution in which (trichloro)(pentamethylcyclopentadienyl)titanium(IV) (376 mg, 1.30 mmol) was dissolved in 5 mL of toluene was slowly dropped thereonto, and reflux was conducted for 24 hours. After the reaction finished, volatile materials were removed, washing was conducted using purified hexane, recrystallization was conducted using a mixed solution of toluene/hexane at −35° C., filtration was conducted, and drying was conducted at reduced pressure to produce 308 mg of red solid component.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureSubsequently, cooling to normal temperature
  3. additionwas slowly dropped
  4. temperaturereflux
  5. customvolatile materials were removed
  6. washwashing
  7. customwas conducted using purified
  8. customhexane, recrystallization
  9. customat −35° C.
  10. filtrationfiltration
  11. customdrying

Sources & evidence

ORD record
ord-41470198c7974cdcb66990adabaf2790
Source dataset
uspto-grants-2009_09
Patent number
US07589042B2

Reaction notes

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