Phenylacetyl chloride → 1-Phenyl-2-hexanone

HRID 1110123Notes

Reaction equation

HRID 1110123 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1>[C:1]1([CH2:7][C:8](=[O:9])[CH2:6][CH2:1][CH2:2][CH3:3])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 7679Phenylacetyl chloride

Product 1

HCID 331911-Phenyl-2-hexanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 ml of n-tetrabutyl tin, then 120 mg of [benzyl (chloro) bis(triphenyl phosphine)]palladium were added to a solution of 40 ml of phenyl acetyl chloride in 500 ml of tetrahydrofuran. The mixture was stirred for 15 hours at reflux, filtered on clarcel and evaporated to dryness. The residue was distilled at 65° C. to 68° C. under 0.5 mm of mercury and the main fraction was chromatographed on silica (eluant: hexane - ethyl acetate (9-1)) to obtain 27.5 g of the desired product.

Workup

  1. temperatureat reflux
  2. filtrationfiltered on clarcel
  3. customevaporated to dryness
  4. distillationThe residue was distilled at 65° C. to 68° C. under 0.5 mm of mercury
  5. customthe main fraction was chromatographed on silica (eluant: hexane - ethyl acetate (9-1))

Sources & evidence

ORD record
ord-6f8cbea72e9d4936bd19c6b52b37701f
Source dataset
uspto-grants-1994_06
Patent number
US05324839

Reaction notes

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