HCID 54452095, compound → HCID 14403422, compound

HRID 1650727Notes

Reaction equation

HRID 1650727 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([C:12]2([Cl:15])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[H][H]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([C:12]2([Cl:15])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 54452095HCID 54452095, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14403422HCID 14403422, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

460 mg (0.5 mmol) of tris-triphenylphosphine rhodium chloride (=1 mol %, with reference to the reaction components) is added to a 100 ml autoclave. After purging with nitrogen, an air-free solution of 12 g (0.05 mol) of 1-chlorocyclopropyl 4-chlorophenylethenyl ketone in 40 ml of toluene is added and heated at 50° C. under a hydrogen pressure of 30 bar. The hydrogen pressure is kept between 40 and 50 bar until the absorption of gas is complete (after about 1 hour). The mixture is subsequently allowed to react for 1 hour. For working up, the solvent is removed under reduced pressure and the residue which remains is purified on silica gel using dichloromethane as the eluant. 11 g (90% of theory) of 1-chlorocyclopropyl 4-chlorophenylethyl ketone are obtained in the form of an oily product.

Workup

  1. additionis added to a 100 ml autoclave
  2. customAfter purging with nitrogen
  3. customuntil the absorption of gas
  4. custom(after about 1 hour)
  5. customto react for 1 hour
  6. customthe solvent is removed under reduced pressure
  7. customthe residue which remains is purified on silica gel

Sources & evidence

ORD record
ord-3f37f04f40f24fdcaddd3bdfa7c49719
Source dataset
uspto-grants-1990_05
Patent number
US04925865

Reaction notes

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