Hydrochloric Acid → Triphenylphosphine

HRID 1970091Notes

Reaction equation

HRID 1970091 reaction equation
[C:1]1([P:7](=[O:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al].C(Cl)(=O)C(Cl)=O.[Pb](Br)Br.Cl>C(#N)C>[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[C:1]1([P:7](=[O:20])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 13097Triphenylphosphine OxideHCID 24831Lead (II) bromideHCID 65578Oxalyl chlorideHCID 5359268Aluminum

Product 2

HCID 11776TriphenylphosphineYield 88%HCID 13097Triphenylphosphine OxideYield 2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine oxide (1.40 g, 5.0 mmol), shredded aluminum foil (136 mg, 5.0 mmol) and acetonitrile (5 mL) were weighted out into a reactor, then oxalyl chloride (0.46 mL, 5.1 mmol) was added thereto under room temperature, and the mixture was stirred at the same temperature for 10 minutes. Subsequently, lead bromide (18 mg, 0.05 mmol) was added to this reaction solution, and the mixture was stirred for 30 minutes at room temperature. Thereafter, the reaction solution was poured into an iced 5% hydrochloric acid aqueous solution from the reactor, to terminate the reaction. The organic layer was separated, and the water layer was extracted with ethyl acetate for 3 times. The organic layers were combined into one, washed with saturated saline, dried on sodium sulfate and concentrated under reduced pressure. The residue was purified with a silica gel column chromatography to give triphenylphosphine (1,162 mg, 4.4 mmol, yield: 88%) and triphenylphosphine oxide (21 mg, 0.07 mmol, collection rate: 2%).

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. customto terminate
  3. customthe reaction
  4. customThe organic layer was separated
  5. extractionthe water layer was extracted with ethyl acetate for 3 times
  6. washwashed with saturated saline
  7. customdried on sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-5a0be7df485a470b87ff2000ca9e55a1
Source dataset
uspto-grants-2013_04
Patent number
US08426629B2

Reaction notes

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