p-Toluenesulfonic acid → HCID 178420720, compound

HRID 1198310Notes

Reaction equation

HRID 1198310 reaction equation
[C:1]1([C:7]2(O)[CH2:11][CH2:10][CH2:9][C:8]2([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23](S(O)(=O)=O)=[CH:22][CH:21]=1.[CH2:31]([Li])[CH2:32][CH2:33][CH3:34].[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[Cl-:42].[Cl-].[Cl-].[Cl-].[Zr+4:46]>C1C=CC=CC=1.O1CCCC1.ClCCl>[Cl-:42].[Cl-:42].[C:1]1([C:7]2([Zr+2:46][C:31]3([C:38]4[CH:37]=[CH:36][CH:41]=[CH:40][CH:39]=4)[CH:32]=[CH:33][CH:34]=[C:30]3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 9856075Zirconium chloride (ZrCl4), (T-4)-HCID 191038931,2-Diphenylcyclopentane-1,2-diolHCID 178418339Butyllithium

Product 1

HCID 178420720HCID 178420720, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2-diphenyl-1,2-cyclopentanediol (1.2 g; 0.0048 mole), activated 4A molecular sieves and a small amount of p-toluenesulphonic acid in 40 ml benzene was heated at 70° C. for 30 minutes. The mixture was filtered at room temperature. A solution (3.0 ml) of n-butyllithium in hexane (1.6 mole/liter, 0.0048 mole n-butyllithium) was added to the filtrate. After 45 minutes of stirring, a solution of zirconium tetrachloride (0.56 g; 0.0024 mole) in tetrahydrofuran was slowly added. After stirring the mixture at 65° C. for three hours, the solvents were evaporated. The solid material obtained was taken up in dichloromethane and centrifuged. The supernatant liquid was decanted and evaporated to dryness. The residue was washed with hexane and crystallized from toluene.

Workup

  1. filtrationThe mixture was filtered at room temperature
  2. stirringAfter stirring the mixture at 65° C. for three hours
  3. customthe solvents were evaporated
  4. customThe solid material obtained
  5. customThe supernatant liquid was decanted
  6. customevaporated to dryness
  7. washThe residue was washed with hexane
  8. customcrystallized from toluene

Sources & evidence

ORD record
ord-221828294b90484f9d5078052f384195
Source dataset
uspto-grants-1994_01
Patent number
US05279999

Reaction notes

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