Hydrochloric Acid → Diphenylphosphine

HRID 2287764Notes

Reaction equation

HRID 2287764 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.Cl.C1(C)C=CC=CC=1>CN(C)C=O.[Zn]>[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 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 66180Chlorodiphenylphosphine

Product 1

HCID 70017DiphenylphosphineYield 63%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

1.04 g (4.71 mmol) of chlorodiphenylphosphine was added dropwise in a nitrogen gas atmosphere to a suspension of 461 mg (7.05 mg-atoms) of zinc (powder) in 10 cm3 of N,N-dimethylformamide and the mixture was stirred at room temperature for one hour. 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 551 mg (2.96 mmol) of diphenylphosphine in 63% 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-134055ee24194d79bf65da68d9a9d55c
Source dataset
uspto-grants-2000_07
Patent number
US06084133

Reaction notes

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