Hydrochloric Acid → Diphenylphosphine

HRID 2287768Notes

Reaction equation

HRID 2287768 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.[Al].Cl.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 313Hydrochloric AcidHCID 1140TolueneHCID 66180ChlorodiphenylphosphineHCID 5359268Aluminum

Product 1

HCID 70017DiphenylphosphineYield 87%

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 127 mg (4.71 mmol) of aluminum (foil) in 10 cm3 of N,N-dimethylformamide and the mixture was stirred at 100° C. for 30 min. To the reaction mixture was added dropwise 10 cm3 (10 mmol) of 1 mol·dm-3 hydrochloric 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 763 mg (4.10 mmol) of diphenylphosphine in 87% 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-6302efb5a3a0430e82a2e37b36cb472f
Source dataset
uspto-grants-2000_07
Patent number
US06084133

Reaction notes

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