Chloride → HCID 14403422, compound

HRID 1650589Notes

Reaction equation

HRID 1650589 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([C:13]2([Cl:16])[CH2:15][CH2:14]2)=[O:12])=[CH:5][CH:4]=1.[H][H]>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([C:13]2([Cl:16])[CH2:15][CH2:14]2)=[O:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 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-triphenylphosphinerhodium chloride (=1 mol %, with respect to the reaction component) are added to a 100 ml autoclave. After purging with nitrogen, an air-free solution of 12 g (0.05 mol) of 1-chlorocyclopropyl 4-chlorophenyl-ethenyl ketone in 40 ml of toluene is added and the mixture is heated to 50° C. under a hydrogen pressure of 30 bar. The hydrogen pressure is held between 40 and 50 bar until gas uptake has ended (after about 1 hour). The mixture is then allowed to react for a further hour. For working up, the solvent is stripped off under reduced pressure and the remaining residue is purified on silica gel using dichloromethane as eluant. 11 g (90% of theory) of 1-chlorocyclopropyl 4-chlorophenylethyl ketone are obtained in the form of an oily product.

Workup

  1. customAfter purging with nitrogen
  2. custom(after about 1 hour)
  3. customto react for a further hour
  4. customthe remaining residue is purified on silica gel

Sources & evidence

ORD record
ord-b00070008c2f47e7869d884b5ebc4636
Source dataset
uspto-grants-1990_05
Patent number
US04925482

Reaction notes

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