(1,1'-Biphenyl)-2-ol → HCID 178425997, compound

HRID 733024Notes

Reaction equation

HRID 733024 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[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:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 178418339ButyllithiumHCID 178425993HCID 178425993, compound

Product 1

HCID 178425997HCID 178425997, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

After 0.86 g of 2-phenylphenol (5.07 mmol) (Aldrich, 99%) were dissolved in 40 mL of toluene, 2.4 mL of butyl lithium (2.5 M hexane solution) were slowly dropped thereonto at 0° C. After the reaction was conducted at normal temperature for 12 hours, a solution in which (trichloro)(pentamethylcyclopentadienyl)titanium(IV) (1.32 g, 4.56 mmol) was dissolved in 10 mL of toluene was slowly dropped thereonto at 0° C. After agitation was conducted at normal temperature for 12 hours, filtration was conducted, volatile materials were removed, and recrystallization was conducted using a mixed solution of toluene/hexane at −35° C. to produce 1.64 g of an orange-colored solid component.

Workup

  1. customat 0° C
  2. additionwas slowly dropped
  3. customat 0° C
  4. waitAfter agitation was conducted at normal temperature for 12 hours
  5. filtrationfiltration
  6. customvolatile materials were removed
  7. customrecrystallization
  8. customat −35° C.

Sources & evidence

ORD record
ord-54e3e95dac694599a75500c173c5ff85
Source dataset
uspto-grants-2009_09
Patent number
US07589042B2

Reaction notes

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