Carbon Tetrachloride → 4,4-Diphenyl-2-cyclopentenyl chloride

HRID 1657279Notes

Reaction equation

HRID 1657279 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH:10](O)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC.C(Cl)(Cl)(Cl)[Cl:45]>C(Cl)Cl>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH:10]([Cl:45])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8058HexaneHCID 11776TriphenylphosphineHCID 108237324,4-Diphenyl-2-cyclopenten-1-ol

Product 1

HCID 107534844,4-Diphenyl-2-cyclopentenyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,4-diphenyl-2-cyclopenten-1-ol (0.30 g), and triphenylphosphine (0.43 g) in carbon tetrachloride (3 ml) was refluxed for 8 hours and cooled. To the mixture was added n-hexane (5 ml), and the mixture was stirred for 10 minutes at room temperature. The insoluble material was filtered off and the filtrate was condensed under reduced pressure. The residue was dissolved in methylene chloride, and to the solution was added silica gel (1 g). After being stirred for 10 minutes, silica gel was filtered off and the filtrate was evaporated in vacuo to give 4,4-diphenyl-2-cyclopentenyl chloride (0.30 g).

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperaturecooled
  3. filtrationThe insoluble material was filtered off
  4. customcondensed under reduced pressure
  5. additionto the solution was added silica gel (1 g)
  6. stirringAfter being stirred for 10 minutes
  7. filtrationsilica gel was filtered off
  8. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-9b75bc65bea9452c9beb5f0be2a637d4
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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