Phosphoric Acid → Diphenylphosphine

HRID 2287770Notes

Reaction equation

HRID 2287770 reaction equation
Cl[P:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Mg].P(=O)(O)(O)O.C1(C)C=CC=CC=1>CN(C)C=O>[C:9]1([PH:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 1140TolueneHCID 66180ChlorodiphenylphosphineHCID 5462224Magnesium

Product 1

HCID 70017DiphenylphosphineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.04 g (4.71 mmol) of chlorodiphenylphosphine was added dropwise under a nitrogen gas atmosphere to a suspension of 229 mg (9.42 mmol) of magnesium (turning) in 10 cm3 of N,N-dimethylformamide and the mixture was stirred at 100° C. for one hour. To the reaction mixture was added dropwise 10 cm3 (10 mmol) of 1 mol·dm-3 phosphoric acid and then 10 cm3 of toluene. The mixture was stirred, the aqueous layer and the toluene layer were separated off, the toluene layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, giving 710 mg (3.81 mmol) of diphenylphosphine in 81% yield.

Workup

  1. stirringThe mixture was stirred
  2. customthe aqueous layer and the toluene layer were separated off
  3. dry with materialthe toluene layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f5512998ed24c58be1f0dbf057c4f51
Source dataset
uspto-grants-2000_07
Patent number
US06084133

Reaction notes

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