O-Cresol → HCID 178425988, compound

HRID 1990695Notes

Reaction equation

HRID 1990695 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([Li])CCC.[Cl-:14].[Cl-].[Cl-].[CH3:17][C:18]1[C:22]([Ti+3:24])([CH3:23])[C:21]([CH3:25])=[C:20]([CH3:26])[C:19]=1[CH3:27]>C1(C)C=CC=CC=1>[Cl-:14].[Cl-:14].[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][Ti+2:24][C:22]1([CH3:23])[C:18]([CH3:17])=[C:19]([CH3:27])[C:20]([CH3:26])=[C:21]1[CH3:25]

Participants

5

Reactant 3

HCID 335O-CresolHCID 178418339ButyllithiumHCID 178425990HCID 178425990, compound

Product 1

HCID 178425988HCID 178425988, compoundYield 165.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.86 g (5.1 mmol) of 2-methylphenol (Aldrich, 99%) was dissolved in 40 ml of toluene, and 2.4 ml of butyllithium (2.5 M hexane solution) was slowly added dropwise thereto. The mixture solution was allowed to react at room temperature for 12 hours, and a solution of (pentamethylcyclopentadienyl)titanium(IV) trichloride (1.64 g, 5.5 mmol) in 10 ml of toluene was slowly added dropwise to the reaction solution at 0° C. The reaction solution was stirred at room temperature for 12 hours, filtered, treated to remove volatile material, and recrystallized with a mixed solution of toluene and hexane at −35° C., thus obtaining 1.64 g of a red solid. The cyclic voltammogram of the catalyst thus prepared is shown in FIG. 2.

Workup

  1. customto react at room temperature for 12 hours
  2. filtrationfiltered
  3. additiontreated
  4. customto remove volatile material
  5. customrecrystallized with a mixed solution of toluene and hexane at −35° C.

Sources & evidence

ORD record
ord-5e347dabe93648faa04ecbb443121510
Source dataset
uspto-grants-2010_01
Patent number
US07645715B2

Reaction notes

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