Phosphine sulfide, triphenyl- → Triphenylphosphine Oxide

HRID 1981073Notes

Reaction equation

HRID 1981073 reaction equation
[C:1]1([P:7](=S)([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.S(Cl)(Cl)=[O:22].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:1]1([P:7](=[O:22])([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

Participants

5

Reactant 3

HCID 19758Phosphine sulfide, triphenyl-HCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of triphenylphosphine sulfide (0.3 g) and ethyl acetate (10 ml) is added thionyl chloride (0.16 ml) at room temperature, and the mixture is stirred for 2 hours at the same temperature. The reaction mixture is shaken with aqueous 6% sodium hydrogen carbonate (20 ml) and the resulting mass is stirred for another 2 hours. The organic layer which forms on standing for a while is taken, washed with water, filtered to remove a solid mass and concentrated to dryness. The residue is crystallized from ether to give triphenylphosphine oxide (0.26 g). m.p. 155°-156° C.

Workup

  1. stirringthe resulting mass is stirred for another 2 hours
  2. washwashed with water
  3. filtrationfiltered
  4. customto remove a solid mass
  5. concentrationconcentrated to dryness
  6. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-3db6450ea7624374b1ac11a52734c717
Source dataset
uspto-grants-1985_04
Patent number
US04511738

Reaction notes

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