Hydrochloric Acid → Triphenylphosphine

HRID 1970093Notes

Reaction equation

HRID 1970093 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 96%HCID 13097Triphenylphosphine OxideYield 2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine oxide (1.40 g, 5.0 mmol), granular aluminum (spherical, φ=3 mm, 2.13 g, 78.9 mmol) and acetonitrile (5 mL) were weighted out into a reactor, then oxalyl chloride (0.46 mL, 5.10 mmol) was added thereto under room temperature, and the mixture was stirred for 10 minutes. Then, lead bromide (17 mg, 0.05 mmol) was added to this reaction solution, and the mixture was stirred for 1 hour under room temperature to cause a reaction. The reaction solution was taken out with a syringe and poured into an iced 5% hydrochloric acid aqueous solution, and further, the granular aluminum was washed with ethyl acetate, and a wash liquid was also poured into the iced 5% hydrochloric acid aqueous solution as well. 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 (1.26 g, 4.82 mmol, yield: 96%) and triphenylphosphine oxide (28 mg, 0.10 mmol, collection rate: 2%) (first reaction).

Workup

  1. stirringthe mixture was stirred for 1 hour under room temperature
  2. customa reaction
  3. customThe reaction solution was taken out with a syringe
  4. washfurther, the granular aluminum was washed with ethyl acetate
  5. additiona wash liquid was also poured into the iced 5% hydrochloric acid aqueous solution as well
  6. customThe organic layer was separated
  7. extractionthe water layer was extracted with ethyl acetate for 3 times
  8. washwashed with saturated saline
  9. customdried on sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-e58feaf45e6d464999c608e7bf6db13f
Source dataset
uspto-grants-2013_04
Patent number
US08426629B2

Reaction notes

Loading…