Acetic Acid → Diphenylphosphine

HRID 2287771Notes

Reaction equation

HRID 2287771 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.C(O)(=O)C.O.C1(C)C=CC=CC=1>CN(C)C=O.[Mn]>[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

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1140TolueneHCID 66180Chlorodiphenylphosphine

Product 1

HCID 70017DiphenylphosphineYield 77.1%

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 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 129 mg (2.35 mmol) of manganese (powder) in 10 cm3 of N,N-dimethylformamide and the mixture was stirred at 100° C. for 6 hours. To the reaction mixture was added dropwise 601 mg (10 mmol) of acetic acid and then 10 cm3 of water and 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 to give 675 mg (3.63 mmol) of diphenylphosphine in 77% 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-d549cb5ed54d4cc5b952ab57feb29f53
Source dataset
uspto-grants-2000_07
Patent number
US06084133

Reaction notes

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