Chloroacetone → 1-(Triphenylphosphoranylidene)acetone

HRID 374622Notes

Reaction equation

HRID 374622 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:21][C:22](=[O:24])[CH3:23]>C(Cl)(Cl)Cl>[C:22]([CH:23]=[P:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:24])[CH3:21]

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 11776Triphenylphosphine

Product 1

HCID 150381-(Triphenylphosphoranylidene)acetoneYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a dried flask, 131.15 g (0.5 mole) of triphenylphosphine and 47.2 g (0.51 mole) of chloroacetone were dissolved in 300 ml of chloroform and heated under reflux for 20 hrs. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was added to 1L of water and 5N sodium hydroxide was added to the mixture. Solid substance thus formed was extracted with methylene chloride, and dried using anhydrous magnesium sulfate. The residue where the organic solvented was removed, was washed with n-hexane and dried under vacuum to give 143.1 g of the title compound(yield: 90%). Chemical analysis was performed to identify the desired compound by 1H-NMR spectroscopy.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hrs
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe residue was added to 1L of water and 5N sodium hydroxide
  5. additionwas added to the mixture
  6. customSolid substance thus formed
  7. extractionwas extracted with methylene chloride
  8. customdried
  9. customThe residue where the organic solvented was removed
  10. washwas washed with n-hexane
  11. customdried under vacuum

Sources & evidence

ORD record
ord-b13a989cf5184fb4a92b7a825aae6418
Source dataset
uspto-grants-1996_01
Patent number
US05481034

Reaction notes

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