p-Toluenesulfonic acid → HCID 178506636, compound

HRID 1198307Notes

Reaction equation

HRID 1198307 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2(O)[CH2:15][CH2:14][CH:13]=[CH:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([Li:32])CCC.CCCCCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([Li:32])[CH:15]=[CH:14][CH:13]=[CH:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 19103907HCID 19103907, compoundHCID 178418339Butyllithium

Product 1

HCID 178506636HCID 178506636, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 7 g of 1-(4-t-butylphenyl)cyclopent-2-en-1-ol (0.032 mole) and 0.1 g of p-toluenesulphonic acid (0.00058 mole) in 70 ml toluene was gently heated to 40° C. for 5 minutes. The mixture was washed with aqueous sodium hydroxide and subsequently with water. After drying the organic phase over magnesium sulphate for 2 hours, 20.3 ml of a solution of n-butyllithium in hexane (1.6 mole/liter, 0.032 mole n-butyllithium) was added. A precipitate was formed and the precipitate was washed three times with hexane to obtain 4-t-butylphenylcyclopentadienyllithium as an off-white solid material.

Workup

  1. washThe mixture was washed with aqueous sodium hydroxide and subsequently with water
  2. dry with materialAfter drying the organic phase over magnesium sulphate for 2 hours
  3. customA precipitate was formed
  4. washthe precipitate was washed three times with hexane

Sources & evidence

ORD record
ord-3d7c06b439d04c1cb85910e249907bab
Source dataset
uspto-grants-1994_01
Patent number
US05279999

Reaction notes

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