Sodium Hydroxide → Triphenylphosphine Oxide

HRID 1981076Notes

Reaction equation

HRID 1981076 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.[OH-:21].[Na+]>C(O)C(C)C>[C:1]1([P:7](=[O:21])([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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19758Phosphine sulfide, triphenyl-

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

To a mixture of isobutanol (50 ml), triphenylphosphine sulfide (7.0 g) and aqueous 5% sodium hydroxide (50 ml) is bubbled chlorine gas at 15° C. until no appreciable amount of the starting sulfide is detected on thin-layer chromatogram. The reaction mixture is allowed to stand for a while and the organic layer is taken. The layer is washed with water and concentrated to dryness. The residue is triturated with ether to give triphenylphosphine oxide.

Workup

  1. customis bubbled chlorine gas at 15° C. until no appreciable amount of the starting sulfide
  2. washThe layer is washed with water
  3. concentrationconcentrated to dryness
  4. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-2f557de74e6549deac7ee1bd7b7f6940
Source dataset
uspto-grants-1985_04
Patent number
US04511738

Reaction notes

Loading…