Sodium hydride → HCID 178425994, compound

HRID 733027Notes

Reaction equation

HRID 733027 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

2-isopropyl-6-phenylphenol (700 mg, 3.28 mmol) and sodium hydride (236 mg, 9.84 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) (930 mg, 3.21 mmol) was dissolved in 5 mL of toluene was slowly dropped thereonto, and reflux was conducted for 24 hours. After the reaction was 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 1.0 g 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-64907b9698754dd2a02357b136aeba52
Source dataset
uspto-grants-2009_09
Patent number
US07589042B2

Reaction notes

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