Phenylacetyl chloride → 1-Phenyl-2-hexanone

HRID 2260826Notes

Reaction equation

HRID 2260826 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-486ebe823b254767abd16ad2a7359734
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Reaction notes

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