Sulfuric Acid → Diphenylphosphine

HRID 2287769Notes

Reaction equation

HRID 2287769 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].S(=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 1118Sulfuric AcidHCID 1140TolueneHCID 66180ChlorodiphenylphosphineHCID 5359268Aluminum

Product 1

HCID 70017DiphenylphosphineYield 84.1%

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 254 mg (9.42 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 sulfuric 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 737 mg (3.96 mmol) of diphenylphosphine in 84% 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-aac97b85626f4d358747c28baa35c74d
Source dataset
uspto-grants-2000_07
Patent number
US06084133

Reaction notes

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