Hydrochloric Acid → Triphenylphosphine

HRID 1970095Notes

Reaction equation

HRID 1970095 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.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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13097Triphenylphosphine OxideHCID 65578Oxalyl chlorideHCID 5359268Aluminum

Product 2

HCID 11776TriphenylphosphineYield 92%HCID 13097Triphenylphosphine OxideYield 0.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine oxide (1.40 g, 5.0 mmol) and acetonitrile (5 mL) were weighted out into a reactor containing the granular aluminum collected after the second reaction, then oxalyl chloride (0.46 mL, 5.10 mmol) was added thereto under room temperature, and the mixture was stirred for 1 hour 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 aluminum granules were 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 (1.22 g, 4.63 mmol, yield: 92%) and triphenylphosphine oxide (10 mg, 0.04 mmol, collection rate: 0.7%) (third reaction).

Workup

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

Sources & evidence

ORD record
ord-5b9f94be73454fa4af95a127c0c2301a
Source dataset
uspto-grants-2013_04
Patent number
US08426629B2

Reaction notes

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