Chlorodiphenylphosphine → Diphenylphosphine

HRID 1287961Notes

Reaction equation

HRID 1287961 reaction equation
[Na].[C:2]1([P:8](Cl)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[C:9]1([PH:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 66180ChlorodiphenylphosphineHCID 5360545Sodium2×

Product 1

HCID 70017DiphenylphosphineYield 76.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
10 °C

Procedure

From Sodium Diphenylphosphide. To a suspension of sodium "sand" (4.6 g, 0.2 g atom) in a 100 ml of anhydrous dioxane heated at 65°-70° C. under nitrogen, a solution of diphenyl phosphorus chloride (22 g., 0.1 ml) in 50 ml of anhydrous dioxane is added during 1 hour. The solution is heated at reflux temperature (100° C) for 4 hours until all of the sodium is consumed. Then, after cooling to 10° C. 30 ml anhydrous ethanol is dropped in, followed by 25 ml of water to dissolve the sodium chloride. The organic layer is separated and the water is extracted with ether. The organic layers are dried and distilled in vacuum giving diphenylphosphine (14.14 g, 76 percent yield).

Workup

  1. temperatureheated at 65°-70° C. under nitrogen
  2. temperatureThe solution is heated
  3. customis consumed
  4. addition30 ml anhydrous ethanol is dropped in,
  5. dissolutionto dissolve the sodium chloride
  6. customThe organic layer is separated
  7. extractionthe water is extracted with ether
  8. customThe organic layers are dried
  9. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-aa86ea7022e146c2896561baab3c96a7
Source dataset
uspto-grants-1976_10
Patent number
US03987009

Reaction notes

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